Phosphorus tribromide → 1-(1-Bromoethyl)-3,5-bis(trifluoromethyl)benzene

HRID 1781295Notes

Reaction equation

HRID 1781295 reaction equation
[F:1][C:2]([F:17])([F:16])[C:3]1[CH:4]=[C:5]([CH:13](O)[CH3:14])[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1.P(Br)(Br)[Br:19]>O>[F:1][C:2]([F:17])([F:16])[C:3]1[CH:4]=[C:5]([CH:13]([Br:19])[CH3:14])[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1

Participants

4

Reactant 2

HCID 24614Phosphorus tribromideHCID 64257391-(3,5-Bis(trifluoromethyl)phenyl)ethanol

Product 1

HCID 129473971-(1-Bromoethyl)-3,5-bis(trifluoromethyl)benzene

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To 1-(3,5-bis(trifiuoromethyl)phenyl)-1-hydroxyethane (10 g) was added phosphorous tribromide (3.7 ml) to give a clear solution. After 30 minutes the solution was added to water (300 ml) and the solution stirred for a further 30 minutes. Petroleum ether bp=60°-80° C. was added and the organic solution washed with water (×3), saturated, NaHCO3, saturated brine and dried (MgSO4). The solution was evaporated in vacuo and the residue distilled b1-4 mm =69° C. to give 1-(3,5-bis(trifluoromethyl)phenyl)-1-bromoethane- 1H NMR (250 MHz; CDCl3) δ7.88 (2H; s; 2,6-arylH), 7.80 (1H; s; 4-arylH), 5.23 (2H,; q, J =6.9 Hz; CH3CH), 2.09 (3H; d, J =6.9 Hz; CH3).

Workup

  1. customto give a clear solution
  2. washthe organic solution washed with water (×3)
  3. dry with materialsaturated, NaHCO3, saturated brine and dried (MgSO4)
  4. customThe solution was evaporated in vacuo
  5. distillationthe residue distilled b1-4 mm =69° C.

Sources & evidence

ORD record
ord-a53056ad25d944aab213571494808620
Source dataset
uspto-grants-1997_05
Patent number
US05633266

Reaction notes

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