Reaction #2507830

Reaction equation

water

triphenylphosphine

bromine

(6-fluoro-3-pentylchroman-7-yl)methanol

→

7-bromomethyl-6-fluoro-3-pentylchroman

Solvents

acetonitrile

acetonitrile

Conditions

Workup

1. 1
   Extractionthe mixture is extracted three times with n-heptane
2. 2
   Washphases are washed with water
3. 3
   Dryingdried over sodium sulfate
4. 4
   OtherThe solvent is removed in vacuo
5. 5
   Filtrationthe residue is filtered through silica gel with heptane/toluene (4:1)

Procedure

10.2 g (38.9 mmol) of triphenylphosphine are suspended in 80 ml of acetonitrile, and 2.0 ml (39.0 mmol) of bromine are added dropwise with ice cooling. A solution of 10.0 g (38.4 mmol) of (6-fluoro-3-pentylchroman-7-yl)methanol in 20 ml of acetonitrile is subsequently added, and the mixture is stirred overnight at room temp. After addition of water, the mixture is extracted three times with n-heptane, and the combined org. phases are washed with water and dried over sodium sulfate. The solvent is removed in vacuo, and the residue is filtered through silica gel with heptane/toluene (4:1), giving 7-bromomethyl-6-fluoro-3-pentylchroman as a colourless oil.

Source