Water → 7-Bromomethyl-6-fluoro-3-pentylchroman

HRID 2420648Notes

Reaction equation

HRID 2420648 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Br:20]Br.[F:22][C:23]1[CH:24]=[C:25]2[C:30](=[CH:31][C:32]=1[CH2:33]O)[O:29][CH2:28][CH:27]([CH2:35][CH2:36][CH2:37][CH2:38][CH3:39])[CH2:26]2.O>C(#N)C>[Br:20][CH2:33][C:32]1[CH:31]=[C:30]2[C:25]([CH2:26][CH:27]([CH2:35][CH2:36][CH2:37][CH2:38][CH3:39])[CH2:28][O:29]2)=[CH:24][C:23]=1[F:22]

Participants

6

Reactant 4

HCID 962WaterHCID 11776TriphenylphosphineHCID 24408BromineHCID 59288346(6-Fluoro-3-pentylchroman-7-yl)methanol

Product 1

HCID 592883307-Bromomethyl-6-fluoro-3-pentylchroman

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

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.

Workup

  1. extractionthe mixture is extracted three times with n-heptane
  2. washphases are washed with water
  3. dry with materialdried over sodium sulfate
  4. customThe solvent is removed in vacuo
  5. filtrationthe residue is filtered through silica gel with heptane/toluene (4:1)

Sources & evidence

ORD record
ord-abd18b9303804278a968543070d90dab
Source dataset
uspto-grants-2011_06
Patent number
US07955664B2

Reaction notes

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