Phosphorus tribromide → 4-(Bromomethyl)-4'-fluoro-1,1'-biphenyl

HRID 2226965Notes

Reaction equation

HRID 2226965 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([CH2:14]O)=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.P(Br)(Br)[Br:17]>CCOCC.O>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([CH2:14][Br:17])=[CH:10][CH:9]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 24614Phosphorus tribromideHCID 1394497[4-(4-Fluorophenyl)phenyl]methanol

Product 1

HCID 189638634-(Bromomethyl)-4'-fluoro-1,1'-biphenyl

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Procedure

To a solution of 4'-fluoro-4-biphenylylmethanol (7.38 g, 36.93 mmol) in Et2O (250 ml) is added phosphorous tribromide (7 ml, 73.06 mmol). The reaction is allowed to warm slowly to room temperature and is then refluxed for 12 hours. After the reaction is cooled to room temperature ice chips are added until gas no longer evolves. The reaction mixture is then diluted with H2O (200 ml) and extracted with 1N NaOH (300 ml) and saturated NaCl solution (300 ml), dried over MgSO4, and concentrated in vacuo to give 4'-fluoro-4-biphenylylmethyl bromide as a white solid.

Workup

  1. temperatureis then refluxed for 12 hours
  2. temperatureAfter the reaction is cooled to room temperature ice chips
  3. additionare added until gas
  4. extractionextracted with 1N NaOH (300 ml) and saturated NaCl solution (300 ml)
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-d4880f3df5544aecaf83923eab5d9a47
Source dataset
uspto-grants-1994_09
Patent number
US05350761

Reaction notes

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