Boron tribromide → HCID 23499550, compound

HRID 1251883Notes

Reaction equation

HRID 1251883 reaction equation
B(Br)(Br)Br.C[O:6][C:7]1[CH:15]=[CH:14][C:10]([C:11]([OH:13])=[O:12])=[C:9]([C:16]2[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=2)[CH:8]=1>ClCCl>[OH:6][C:7]1[CH:15]=[CH:14][C:10]([C:11]([OH:13])=[O:12])=[C:9]([C:16]2[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=2)[CH:8]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 23499547HCID 23499547, compound

Product 1

HCID 23499550HCID 23499550, compoundYield 66.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

A solution of boron tribromide (0.066 mol) in dichloromethane (66 ml) was added dropwise to a solution of 4-methoxy-2-(4-fluorophenyl)benzoic acid (7.7 g; 0.029 mol) in dried dichloromethane (215 ml) under argon at 0° C. The reaction was stirred for 1 hour at 0° C. and allowed to warm to ambient temperature and stirred for a further 16 hours. It was then poured into ice water and extracted with firstly dichloromethane then with ethyl acetate. The combined organic extracts were washed with saturated aqueous sodium hydrogen carbonate and the aqueous phase acidified to pH 1 with concentrated HCl and extracted with ethyl acetate. The ethyl acetate extracts were dried (MgSO4) and concentrated in vacuo to give 4-hydroxy-2-(4-fluorophenyl)benzoic acid as a yellow oil (4.5 g), which was used without further purification.

Workup

  1. temperatureto warm to ambient temperature
  2. stirringstirred for a further 16 hours
  3. extractionextracted with firstly dichloromethane
  4. washThe combined organic extracts were washed with saturated aqueous sodium hydrogen carbonate
  5. extractionextracted with ethyl acetate
  6. dry with materialThe ethyl acetate extracts were dried (MgSO4)
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-149956218e0942a28bbfb0d6e90e2936
Source dataset
uspto-grants-2002_01
Patent number
US06342765B1

Reaction notes

Loading…