Phosphorus tribromide → 4-Bromomethyl-2,6-dimethyl-4'-trifluoromethyl-biphenyl

HRID 251309Notes

Reaction equation

HRID 251309 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([CH2:8]O)[CH:5]=[C:4]([CH3:10])[C:3]=1[C:11]1[CH:16]=[CH:15][C:14]([C:17]([F:20])([F:19])[F:18])=[CH:13][CH:12]=1.P(Br)(Br)[Br:22]>C1COCC1>[Br:22][CH2:8][C:6]1[CH:7]=[C:2]([CH3:1])[C:3]([C:11]2[CH:16]=[CH:15][C:14]([C:17]([F:20])([F:19])[F:18])=[CH:13][CH:12]=2)=[C:4]([CH3:10])[CH:5]=1

Participants

4

Reactant 2

HCID 24614Phosphorus tribromideHCID 67485876HCID 67485876, compound

Product 1

HCID 674861454-Bromomethyl-2,6-dimethyl-4'-trifluoromethyl-biphenylYield 81.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of (2,6-dimethyl-4′-trifluoromethyl-biphenyl-4-yl)-methanol (2.22 g, 7.9 mmol) in THF (30 ml) is added PBr3 (3.22 g, 11.9 mmol) in THF (5 ml) and the reaction is allowed to stir at room temperature for about 2 h. The reaction is cooled to 0° C. and ice water is added slowly. The mixture is extracted with ethyl acetate, dried over MgSO4, and concentrated. The resulting residue is purified by silica gel column chromatography, eluting with EtOAc/hexanes to afford 2.2 g of the titled compound as a white solid. 1H-NMR.

Workup

  1. temperatureThe reaction is cooled to 0° C.
  2. extractionThe mixture is extracted with ethyl acetate
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated
  5. customThe resulting residue is purified by silica gel column chromatography
  6. washeluting with EtOAc/hexanes

Sources & evidence

ORD record
ord-ca9b35e2ff434e9289f4c5e40d6eda67
Source dataset
uspto-grants-2011_01
Patent number
US07863329B2

Reaction notes

Loading…