Boron tribromide → 2-Phenoxy-5-trifluoromethyl-phenol

HRID 1822331Notes

Reaction equation

HRID 1822331 reaction equation
[O:1]([C:8]1[CH:13]=[CH:12][C:11]([C:14]([F:17])([F:16])[F:15])=[CH:10][C:9]=1[O:18]C)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.B(Br)(Br)Br>C(Cl)Cl>[O:1]([C:8]1[CH:13]=[CH:12][C:11]([C:14]([F:15])([F:16])[F:17])=[CH:10][C:9]=1[OH:18])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 690780152-Phenoxy-5-trifluoromethyl-anisole

Product 1

HCID 578942142-Phenoxy-5-trifluoromethyl-phenolYield 36%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

A −78° C. solution of the crude 2-phenoxy-5-trifluoromethyl-anisole (3.79 g, 14.1 mmol) in CH2Cl2 (38 mL) is treated with BBr3 (14.04 g, 56.1 mmol) and then warmed to 0° C. The mixture is stirred for 1.5 h under N2, poured into ice water and extracted with Et2O. The organic layer is dried (Na2SO4), and the solvent is removed in vacuo to afford crude material that is absorbed on silica gel and columned with 6/1 hexanes/ethyl acetate to afford 1.29 g (18%) of the title compound. 1H NMR (400 MHz, CDCl3); MS (ES−+) m/z mass calculated for C13H9O2F3 254, found 253 (M+1, 100%).

Workup

  1. extractionextracted with Et2O
  2. dry with materialThe organic layer is dried (Na2SO4)
  3. customthe solvent is removed in vacuo
  4. customto afford crude material that
  5. customis absorbed on silica gel

Sources & evidence

ORD record
ord-bf9babe9d5ae435c96386f7ad7fc3171
Source dataset
uspto-grants-2009_10
Patent number
US07608639B2

Reaction notes

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