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CAS No. : | 698-19-1 | MDL No. : | MFCD05262953 |
Formula : | C8H10BrN | Boiling Point : | No data available |
Linear Structure Formula : | - | InChI Key : | TUADRPBKJHMHDH-UHFFFAOYSA-N |
M.W : | 200.08 | Pubchem ID : | 522360 |
Synonyms : |
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Signal Word: | Warning | Class: | |
Precautionary Statements: | P305+P351+P338 | UN#: | |
Hazard Statements: | H302-H319 | Packing Group: | |
GHS Pictogram: |
* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
95% | In tetrahydrofuran; at 20℃; for 16h; | Preparation of ferf-butyl 2-bromobenzyl(methyl)carbamate (59). 58 59 A solution of compound 58 (2.0 g, 10.0 mmol) and Boc20 (2.29 g, 10.5 mmol) in THF (40 mL) was stirred at RT for 16 hours. The mixture was then concentrated in vacuo. The crude product was purified by flash column chromatography over silica gel, which was eluted with 10% EtOAc in heptanes, and yielded compound 59 as a colorless oil (2.8 g, 95% yield). 1H NMR (400 MHz, CDCI3) δ 7.54 (d, 1 H), 7.30 (t, 1 H), 7.13 (m, 2 H), 4.53 (br d, 2 H), 2.87 (br s, 3 H), 1.46 (br d, 9 H). |
76.9% | In tetrahydrofuran; at 25℃; for 1h; | [0178] Step A: To a mixture of N-(2-bromophenyl)-N-methylmethanamine (6.50 g, 32.5 mmol, 1 eq .) in THF (R.0 mL) was added B0C2O (R80 g, 35.7 mmol, 8.21 mL, 1,10 eq.) dropwise at 25 C, and the mixture was stirred at 25 C for 1 hour. The reaction mixture was directly concentrated in vacuo to give a residue. The residue was purified by column chromatography (S1O2, petroleum ether/ethyl acetate = 20/1 to 10/1) to give tert-butyl (2-bromobenzyl)(methyl)carbamate (R50 g, 25.0 mmol, 76.9% yield) as a colorless oil. [0179] NMR (400 MHz, CDCb) d 7.55 (br d , J= 8.0 Hz, 1H), 7.34 -7.28 (m, 1H), 7.22-7.08 (m, 2H), 4.61-4.42 (m, 2H), 2.94 -2.78 (m, 3H), 1.60 -1.33 (m, 9H). |
76.9% | In tetrahydrofuran; at 25℃; for 1h; | To a mixture of l-(2-bromophenyl)-N-methylmethanamine (6.50 g, 32.5 mmol, 1 eq.) in THF (70.0 mL) was added B0C2O (7.80 g, 35.7 mmol, 8.21 mL, 1.10 eq.) dropwise at 25 C, and the mixture was stirred at 25 C for 1 hour. The reaction mixture was directly concentrated in vacuo to give a residue. The residue was purified by column chromatography (SiO2, petroleum ether/ethyl acetate = 20/1 to 10/1) to give tert- butyl (2- bromobenzyl)(methyl)carbamate (7.50 g, 25.0 mmol, 76.9% yield) as a colorless oil. (0179) [0165] 1H NMR (400 MHz, CDCb) d 7.55 (br d, J= 8.0 Hz, 1H), 7.34 - 7.28 (m, 1H), 7.22 - (0180) 7.08 (m, 2H), 4.61 - 4.42 (m, 2H), 2.94 - 2.78 (m, 3H), 1.60 - 1.33 (m, 9H). |
76.9% | In tetrahydrofuran; at 25℃; for 1h; | To a mixture of 1-(2-bromophenyl)-N-methylmethanamine (6.50 g, 32.5 mmol, 1 eq.) in THF (70.0 mL) was added Boc2O (7.80 g, 35.7 mmol, 8.21 mL, 1.10 eq.) dropwise at 25 C, and the mixture was stirred at 25 C for 1 hour. The reaction mixture was directly concentrated in vacuo to give a residue. The residue was purified by column chromatography (SiO2, petroleum ether/ethyl acetate = 20/1 to 10/1) to give tert-butyl (2-bromobenzyl)(methyl)carbamate (7.50 g, 25.0 mmol, 76.9% yield) as a colorless oil. 1H NMR (400 MHz, CDCl3) δ 7.55 (br d, J = 8.0 Hz, 1H), 7.34 - 7.28 (m, 1H), 7.22 -7.08 (m, 2H), 4.61 - 4.42 (m, 2H), 2.94 - 2.78 (m, 3H), 1.60 - 1.33 (m, 9H). |
76.9% | In tetrahydrofuran; at 25℃; for 1h; | To a mixture of 1-(2-bromophenyl)-N-methylmethanamine (6.50 g, 32.5 mmol, 1 eq.) in THF (70.0 mL) was added Boc2O (7.80 g, 35.7 mmol, 8.21 mL, 1.10 eq.) dropwise at 25 C, and the mixture was stirred at 25 C for 1 hour. The reaction mixture was directly concentrated in vacuo to give a residue. The residue was purified by column chromatography (SiO2, petroleum ether/ethyl acetate = 20/1 to 10/1) to give tert-butyl (2-bromobenzyl)(methyl)carbamate (7.50 g, 25.0 mmol, 76.9% yield) as a colorless oil. 1H NMR (400 MHz, CDCl3) δ 7.55 (br d, J = 8.0 Hz, 1H), 7.34 - 7.28 (m, 1H), 7.22 -7.08 (m, 2H), 4.61 - 4.42 (m, 2H), 2.94 - 2.78 (m, 3H), 1.60 - 1.33 (m, 9H). |
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