Boron tribromide → HCID 23499550, compound

HRID 1836425Notes

Reaction equation

HRID 1836425 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 62%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

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

Workup

  1. temperatureto warm to ambient temperature
  2. stirringstirred for 16 hours
  3. extractionextracted with 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
  7. customevaporated to dryness

Sources & evidence

ORD record
ord-dc97306edac84c7e97ba3de359031ebc
Source dataset
uspto-grants-2004_08
Patent number
US06777438B2

Reaction notes

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