4-Fluoro-2-(hydroxymethyl)phenol → (5-Fluoro-2-hydroxybenzyl)(triphenyl)phosphonium bromide

HRID 1015926

Reaction equation

HRID 1015926 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[C:4]([CH2:9]O)[CH:3]=1.[BrH:11].[C:12]1([PH+:18]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>C(#N)C>[Br-:11].[F:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[C:4]([CH:3]=1)[CH2:9][P+:18]([C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1)([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1

Participants

4

Reactant 2

HCID 106068384-Fluoro-2-(hydroxymethyl)phenolHCID 22178555Triphenylphosphonium hydrobromide

Product 1

HCID 86638793(5-Fluoro-2-hydroxybenzyl)(triphenyl)phosphonium bromide

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

In 186 ml of acetonitrile, 18.6 g (130.87 mmol) of 4-fluoro-2-(hydroxymethyl)phenol and 42.67 g (124.32 mmol) of triphenylphosphonium hydrobromide are stirred under reflux for 3 h. After cooling, the precipitate formed is filtered off with suction and dried. This gives 58 g (124 mmol, 100% of theory) of the title compound.

Workup

  1. temperatureunder reflux for 3 h
  2. temperatureAfter cooling
  3. customthe precipitate formed
  4. filtrationis filtered off with suction
  5. customdried

Sources & evidence

ORD record
ord-76c9457c1212430b9ee04f3077ce7db9
Source dataset
uspto-grants-2011_07
Patent number
US07985876B2

Linked notes

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