Phosphorus tribromide → 1-(1-Bromoethyl)-3-methylbenzene

HRID 2206542

Reaction equation

HRID 2206542 reaction equation
P(Br)(Br)[Br:2].[C:5]1([CH3:14])[CH:10]=[CH:9][CH:8]=[C:7]([CH:11](O)[CH3:12])[CH:6]=1>>[Br:2][CH:11]([C:7]1[CH:8]=[CH:9][CH:10]=[C:5]([CH3:14])[CH:6]=1)[CH3:12]

Participants

3

Procedure

Phosphorus tribromide (4.28 g, 15.9 mmol) was added drop-wise to a stirred neat solution of 1-(m-tolyl)ethanol (0.9 g, 6.6 mmol) at 0° C. After being stirred to room temperature over 12 h, the reaction was carefully quenched with sat'd saturated aqueous NaHCO3 solution and the mixture was extracted with EtOAc. The organic extract was washed with water, dried with MgSO4, and conc. in vacuo to afford the title compound (1.2 g, 91%) as a colorless oil, that was used directly in the next step without further purification. LCMS 200 (M+H+).

Workup

  1. customthe reaction was carefully quenched with sat'd saturated aqueous NaHCO3 solution
  2. extractionthe mixture was extracted with EtOAc
  3. extractionThe organic extract
  4. washwas washed with water
  5. dry with materialdried with MgSO4

Sources & evidence

ORD record
ord-c35aa29ec8ad4d20905cedd6519d2cca
Source dataset
uspto-grants-2016_06
Patent number
US09371331B2

Linked notes

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