ChemicalBook CAS DataBase List 1-broMo-4-phthaldehyde

1-broMo-4-phthaldehyde synthesis

10synthesis methods

Product Name:1-broMo-4-phthaldehyde
CAS Number:50672-84-9
Molecular formula:C11H7BrO
Molecular Weight:235.08

16650-55-8
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$12.00/1g

50672-84-9
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$7.00/100mg

Yield: 78%

Reaction Conditions:

Stage #1:4-bromonaphthalene-1-carboxylic acid with diborane in tetrahydrofuran at 0 - 25; for 5 h;Inert atmosphere;
Stage #2: with sodium hydrogencarbonate;Dess-Martin periodane in tetrahydrofuran;dichloromethane at 0; for 4 h;Inert atmosphere;

Steps:

3.2.1 4-Bromo-1-naphthaldehyde (7)
BH3 (40.0 mL, 1 mol L-1) was added to a solution of 7a (5.0 g, 20.0 mmol) in dry THF (50.0 mL) at 0°C, and the mixture stirred at room temperature for 5 h. The reaction was quenched with a saturated aqueous solutionof NH4Cl and concentrated under vacuum. The aqueous residue was extracted with EtOAc (3 × 200.0 mL). The combined organic layers were dried over Na2SO4 and concentrated under vacuum. The residue was used in the next step without purification. Dess-Martin reagent (8.5 g, 20.0 mmol) and NaHCO3 (5.0 g, 60.0 mmol) were added to a solution of the residue in CH2Cl2 (150.0 mL) at 0°C. The reaction mixture was stirred at 0°C for 4 h, H2O(200.0 mL) was added, and the mixture was extracted with CH2Cl2 (3 × 200.0 mL). The combined organic layer was concentrated under vacuum. The residue was purified by chromatography (EtOAc/hexanes = 1:20) to afford the compound 7 (yield 3.6 g, 78%) as a colorless solid; m.p. 79-81°C. 1H NMR (400 MHz, CDCl3): δ = 10.36 (s, 1H,-CHO), 9.27 (d, J = 8.4 Hz, 1H, Ar-H), 8.35 (d, J = 8.4 Hz, 1H,Ar-H), 7.95 (d, J = 7.6 Hz, 1H, Ar-H), 7.79 (d, J = 7.6 Hz, 1H,Ar-H), 7.69-7.75 (m, 2H, Ar-H). 13C NMR (100 MHz, CDCl3):δ = 192.6, 136.1, 132.1, 131.4, 131.3, 130.9, 129.8, 129.3, 128.3,127.7, 125.1. HRMS ((+)-ESI): m/z = 234.9731. (calcd. 234.9753 for C11H7BrO, [M + H]+).

References:

Li, Xiaowan;Si, Tongxu;Ku, Chuenfai;Zhang, Hongjie;Wang, Mingzhong;Chan, Albert S.C. [Zeitschrift fur Naturforschung, B: Chemical Sciences,2019,vol. 74,# 2,p. 183 - 189]

79996-99-9 Synthesis