Phosphorus tribromide → 3-(Bromomethyl)-2,4-difluorophenol

HRID 1179273Notes

Reaction equation

HRID 1179273 reaction equation
[F:1][C:2]1[C:7]([CH2:8]O)=[C:6]([F:10])[CH:5]=[CH:4][C:3]=1[OH:11].P(Br)(Br)[Br:13]>C(OCC)C>[Br:13][CH2:8][C:7]1[C:2]([F:1])=[C:3]([OH:11])[CH:4]=[CH:5][C:6]=1[F:10]

Participants

4

Reactant 2

HCID 24614Phosphorus tribromideHCID 451191212,4-Difluoro-3-(hydroxymethyl)phenol

Product 1

HCID 692645783-(Bromomethyl)-2,4-difluorophenolYield 47%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a stirred solution of 2,4-difluoro-3-(hydroxymethyl)phenol (step 1, 410 mg, 256 mmol) in diethyl ether (4 mL) and dichloromethne (1 mL) was added phosphorus tribromide (0.257 mL, 2.71 mmol) at 0° C. The mixture was stirred for 30 min, and then the mixture was poured onto ice-aqueous sodium bicarbonate. The mixture was extracted with ethyl acetate (200 mL), and the organic layer was washed with water and brine, dried over magnesium sulfate and evapolated to afford 266 mg (47%) of the title compound as a colorless oil, which was used in the next step without purification:

Workup

  1. additionthe mixture was poured onto ice-aqueous sodium bicarbonate
  2. extractionThe mixture was extracted with ethyl acetate (200 mL)
  3. washthe organic layer was washed with water and brine
  4. dry with materialdried over magnesium sulfate

Sources & evidence

ORD record
ord-24398224da1845f48aca480044b72774
Source dataset
uspto-grants-2007_10
Patent number
US07279486B2

Reaction notes

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