Phosphorus tribromide → Benzene, 2-(bromomethyl)-1,3-dichloro-5-(trifluoromethyl)-

HRID 2235194Notes

Reaction equation

HRID 2235194 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:5]=[C:4]([Cl:12])[C:3]=1[CH2:13]O.P(Br)(Br)[Br:16].C(=O)(O)[O-].[Na+]>C1COCC1>[Br:16][CH2:13][C:3]1[C:2]([Cl:1])=[CH:7][C:6]([C:8]([F:11])([F:10])[F:9])=[CH:5][C:4]=1[Cl:12]

Participants

5

Reactant 3

HCID 24614Phosphorus tribromideHCID 516892Sodium BicarbonateHCID 66652749(2,6-Dichloro-4-(trifluoromethyl)phenyl)methanol

Product 1

HCID 22235045Benzene, 2-(bromomethyl)-1,3-dichloro-5-(trifluoromethyl)-Yield 162.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

Dissolve (2,6-dichloro-4-trifluoromethyl-phenyl)-methanol (7.5 g, 31 mmol) is THF (40 mL) and cool to 0° C. Add PBr3 (5.0 g, 18 mmol) under nitrogen and stir at 0° C. for 30 minutes. Pour into saturated aqueous sodium bicarbonate and extract with methylene chloride. Dry over sodium sulfate, filter and concentrate. Purify over silica gel (hexanes) to obtain 9.0 g (96%) of the title compound.

Workup

  1. extractionextract with methylene chloride
  2. dry with materialDry over sodium sulfate
  3. filtrationfilter
  4. concentrationconcentrate
  5. customPurify over silica gel (hexanes)

Sources & evidence

ORD record
ord-4e7d762e1f98408c9d5a2ce4a7da6463
Source dataset
uspto-grants-2010_05
Patent number
US07713979B2

Reaction notes

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