Boron tribromide → 2-(2,3-Difluoro-4-hydroxyphenyl)acetic acid

HRID 1689395Notes

Reaction equation

HRID 1689395 reaction equation
B(Br)(Br)Br.[F:5][C:6]1[C:11]([F:12])=[C:10]([O:13]C)[CH:9]=[CH:8][C:7]=1[CH2:15][C:16]([OH:18])=[O:17]>C(Cl)Cl>[F:5][C:6]1[C:11]([F:12])=[C:10]([OH:13])[CH:9]=[CH:8][C:7]=1[CH2:15][C:16]([OH:18])=[O:17]

Participants

4

Reactant 2

HCID 25134Boron tribromide2×HCID 177508122,3-Difluoro-4-methoxyphenylacetic acid

Product 1

HCID 299221072-(2,3-Difluoro-4-hydroxyphenyl)acetic acid

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of boron tribromide (1M in DCM, 13.4 mL) was added dropwise to suspension of 2-(2,3-difluoro-4-methoxyphenyl)acetic acid (1.18 g) in DCM (5 mL) at −78° C. The reaction was allowed to warm to RT and stirred overnight. The reaction was cooled to −78° C. and a solution of boron tribromide (1M in DCM, 13.4 mL) was added. The reaction was allowed to warm to RT and stirred for 1 h. The reaction was poured onto ice. The resulting aqueous solution was extracted with DCM (5×50 mL). The aqueous phase was then extracted with ethyl acetate (3×100 mL). The organic solutions were combined, washed with brine (50 mL), dried over magnesium sulphate, filtered and evaporated to give the subtitled compound as a tan solid. Yield 1.09 g.

Workup

  1. temperatureThe reaction was cooled to −78° C.
  2. temperatureto warm to RT
  3. stirringstirred for 1 h
  4. additionThe reaction was poured onto ice
  5. extractionThe resulting aqueous solution was extracted with DCM (5×50 mL)
  6. extractionThe aqueous phase was then extracted with ethyl acetate (3×100 mL)
  7. washwashed with brine (50 mL)
  8. dry with materialdried over magnesium sulphate
  9. filtrationfiltered
  10. customevaporated

Sources & evidence

ORD record
ord-b5f9c08dbc4b4dda962f80523dfd1eae
Source dataset
uspto-grants-2012_04
Patent number
US08148373B2

Reaction notes

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