Boron tribromide → 2-(2,2,2-Trifluoroethoxy)phenol

HRID 1261795Notes

Reaction equation

HRID 1261795 reaction equation
B(Br)(Br)Br.C[O:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[O:13][CH2:14][C:15]([F:18])([F:17])[F:16]>C(Cl)Cl>[F:16][C:15]([F:17])([F:18])[CH2:14][O:13][C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=1[OH:6]

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 200943441-Methoxy-2-(2,2,2-trifluoroethoxy)benzene

Product 1

HCID 130853472-(2,2,2-Trifluoroethoxy)phenolYield 69.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Boron tribromide (2.8 ml, 0.03 mole) was added to a solution of 1-methoxy-2-(2,2,2-trifluoroethoxy)benzene (X) (6.0 g, 0.03 mole) in methylene chloride (90 ml) with stirring below −10° C. Reaction was stirred at −10 to −20° C. for 30 minutes. The reaction mixture was quenched using aqueous sodium bicarbonate solution. Organic layer was separated, washed with water and dried over sodium sulphate. The solvent was evaporated under reduced pressure to give 4.0 g of (XI) as oil. Purity (by GC)=95%.

Workup

  1. customReaction
  2. stirringwas stirred at −10 to −20° C. for 30 minutes
  3. customThe reaction mixture was quenched
  4. customOrganic layer was separated
  5. washwashed with water
  6. dry with materialdried over sodium sulphate
  7. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-7da96f2b51c34ee3bee620c35412cf01
Source dataset
uspto-grants-2013_06
Patent number
US08471039B2

Reaction notes

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