Boron tribromide → 2-Phenoxy-3-trifluoromethyl-phenol

HRID 1822328Notes

Reaction equation

HRID 1822328 reaction equation
[O:1]([C:8]1[C:13]([C:14]([F:17])([F:16])[F:15])=[CH:12][CH:11]=[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[C:13]([C:14]([F:15])([F:16])[F:17])=[CH:12][CH:11]=[CH:10][C:9]=1[OH:18])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 690761002-Phenoxy-3-trifluoromethyl-anisole

Product 1

HCID 541728522-Phenoxy-3-trifluoromethyl-phenolYield 46%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

A −78° C. solution of the crude 2-phenoxy-3-trifluoromethyl-anisole (3.47 g, 12.9 mmol) in CH2Cl2 (35 mL) is treated with BBr3 (12.99 g, 51.8 mmol), and the mixture is warmed to 0° C. and stirred for 1.5 h under N2. The reaction is poured into ice water and then 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 96/4 chloroform/methyl tert-butyl ether to afford 1.51 g (24%) of 2-phenoxy-3-trifluoromethyl-phenol. Rf=0.34 (96/4 chloroform/methyl tert-butyl ether). 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-924a77610ca34f3e91deb041e08a6521
Source dataset
uspto-grants-2009_10
Patent number
US07608639B2

Reaction notes

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