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

HRID 899245Notes

Reaction equation

HRID 899245 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.ClCCl>[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

5

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 2,4-difluoro-3-(hydroxymethyl)phenol (step 1, 410 mg, 256 mmol) in diethyl ether (4 mL) and dichloromethane (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 washed with water and brine, dried over magnesium sulfate and evaporated 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 washed with water and brine
  4. dry with materialdried over magnesium sulfate
  5. customevaporated

Sources & evidence

ORD record
ord-9a64de11d1444a81b758acf607c3eebc
Source dataset
uspto-grants-2008_04
Patent number
US07354925B2

Reaction notes

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