ChemicalBook CAS DataBase List 7-(Bromomethyl)-1-benzofuran

7-(Bromomethyl)-1-benzofuran synthesis

5synthesis methods

Product Name:7-(Bromomethyl)-1-benzofuran
CAS Number:95333-19-0
Molecular formula:C9H7BrO
Molecular Weight:211.06

209256-55-3
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95333-19-0
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$447.00/1g

Yield:95333-19-0 90%

Reaction Conditions:

Stage #1: benzofuran-7-ylmethanolwith methanesulfonyl chloride;triethylamine in dichloromethane at 0; for 1 h;
Stage #2: with lithium bromide in acetone; for 0.5 h;Reflux;

Steps:

7-(Bromomethyl)benzofuran (170)

A solution of 169 (4.72 g, 31.8 mmol) in DCM (100 mL, anhydrous) at 0 °C was treated sequentially with triethylamine (8.9 mL, 63.9 mmol) then mesyl chloride (3.70 mL, 47.8 mmol), the mixture was stirred at 0 °C for 1 h then partitioned between DCM and water. The organic fraction was dried and evaporated and the residue was dissolved in acetone (200 mL), LiBr (27.6 g, 318 mmol) was added and the mixture was refluxed for 0.5 h and then evaporated. The residue was partitioned between DCM and water; the organic fraction was dried and evaporated. Column chromatography (DCM) gave 170 (6.08 g, 90%). 1H MR (CDC1₃) δ 7.69 (d, J = 2.2 Hz, 1H), 7.57 (dd, J = 7.7, 1.2 Hz, 1H), 7.32 (dd, J = 7.4, 0.7 Hz, 1H), 7.22 (t, J = 7.6 Hz, 1H), 6.80 (d, J = 2.2 Hz, 1H), 4.81 (s, 2H).

References:

WO2017/155909,2017,A1 Location in patent:Paragraph 0228