Benzyl Bromide → 2-Benzyloxy-5-(trifluoromethoxy)bromobenzene

HRID 582468Notes

Reaction equation

HRID 582468 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([O:8][C:9]([F:12])([F:11])[F:10])[CH:5]=[CH:4][C:3]=1[OH:13].C(=O)([O-])[O-].[K+].[K+].[CH2:20](Br)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>CN(C)C=O.O>[CH2:20]([O:13][C:3]1[CH:4]=[CH:5][C:6]([O:8][C:9]([F:11])([F:12])[F:10])=[CH:7][C:2]=1[Br:1])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

6

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 215840902-Bromo-4-(trifluoromethoxy)phenol

Product 1

HCID 112909662-Benzyloxy-5-(trifluoromethoxy)bromobenzeneYield 96.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

2-Bromo-4-(trifluoromethoxy)phenol (Preparation 8; 5 g, 20 mmol) was dissolved in N,N-dimethylformamide (60 ml), and potassium carbonate (5.4 g, 40 mmol) was added, followed by benzyl bromide (3.5 ml, 30 mmol), and the reaction was stirred at ambient temperature for 15 hours. The reaction was diluted with water (150 ml) and extracted into ethyl acetate (3×60 ml). The combined organic fractions were washed with water (100 ml), brine (100 ml), dried (MgSO4) and evaporated in vacuo. Purification on silica, eluting with 2% and 5% ethyl acetate in hexane gave the title compound as a clear oil (6.7 g, 96%). 1H NMR (250 MHz, CDCl3) δ 5.47 (2H, s), 7.23 (1H, d, J=9 Hz), 7.43 (1H, dd J=8.2, 2.9 Hz), and 7.75 (6H, m).

Workup

  1. extractionextracted into ethyl acetate (3×60 ml)
  2. washThe combined organic fractions were washed with water (100 ml), brine (100 ml)
  3. dry with materialdried (MgSO4)
  4. customevaporated in vacuo
  5. customPurification on silica
  6. washeluting with 2% and 5% ethyl acetate in hexane

Sources & evidence

ORD record
ord-e33b04516a11458e812a2f291895ba92
Source dataset
uspto-grants-1999_07
Patent number
US05925627

Reaction notes

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