Boron tribromide → 2-Hydroxy-5-(trifluoromethoxy)phenylboronic acid

HRID 2283639Notes

Reaction equation

HRID 2283639 reaction equation
C[O:2][C:3]1[CH:8]=[CH:7][C:6]([O:9][C:10]([F:13])([F:12])[F:11])=[CH:5][C:4]=1[B:14]([OH:16])[OH:15].B(Br)(Br)Br>ClCCl>[OH:2][C:3]1[CH:8]=[CH:7][C:6]([O:9][C:10]([F:13])([F:11])[F:12])=[CH:5][C:4]=1[B:14]([OH:16])[OH:15]

Participants

4

Reactant 2

HCID 25134Boron tribromide2×HCID 222491602-Methoxy-5-(trifluoromethoxy)phenylboronic acid

Product 1

HCID 666556152-Hydroxy-5-(trifluoromethoxy)phenylboronic acidYield 96.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

A suspension of 2-methoxy-5-(trifluoromethoxy)phenylboronic acid (23.0 g, 97.5 mmol) in dichloromethane (140 mL) was cooled to 0° C. and boron tribromide (9.4 mL, 10 mmol) was added drop-wise over 30 min. After stirring for 3 hours, additional boron tribromide (2 mL) was added. The reaction mixture was poured into ice water and stirred for 20 min. The dichloromethane was removed in vacuo and the white solid collected by filtration and washed with water before drying in vacuo to afford the title compound (20.8 g).

Workup

  1. stirringstirred for 20 min
  2. customThe dichloromethane was removed in vacuo
  3. filtrationthe white solid collected by filtration
  4. washwashed with water
  5. custombefore drying in vacuo

Sources & evidence

ORD record
ord-595b9cc25da649e1960bdf82ccb64975
Source dataset
uspto-grants-2015_09
Patent number
US09145407B2

Reaction notes

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