Reaction #43451

Reaction equation

2,3-dihydro-1-benzofuran-5-carbaldehyde

sodium acetate

bromine

→

desired compound

Yield 91.3%

7-bromo-2,3-dihydro-1-benzofuran-5-carbaldehyde

Yield 91.3%

Solvents

acetic acid

sodium thiosulfate

Conditions

Workup

1. 1
   Washwashed with a saturated aqueous solution of sodium bicarbonate
2. 2
   Extractionextracted with ethyl acetate
3. 3
   Dryingdried over sodium sulfate
4. 4
   Otherdried in vacuo

Procedure

To a solution of 2,3-dihydro-1-benzofuran-5-carbaldehyde (1.0 g, 6.75 mmol) in glacial acetic acid (8 ml) was added sodium acetate (664 mg, 8.1 mmol) and bromine (0.7 ml, 13.5 mmol) at 10° C. slowly. The reaction was stirred for 2 h at room temperature. The reaction was diluted with a saturated aqueous solution of sodium thiosulfate (10 ml), washed with a saturated aqueous solution of sodium bicarbonate, and then extracted with ethyl acetate. Organics were combined, dried over sodium sulfate and dried in vacuo to give the desired compound (1.4 g, 91%).

Source