Methanol → 2,3-Difluoro-6-hydroxybenzaldehyde

HRID 1584894Notes

Reaction equation

HRID 1584894 reaction equation
B(Br)(Br)Br.[F:5][C:6]1[C:13]([F:14])=[CH:12][CH:11]=[C:10]([O:15]C)[C:7]=1[CH:8]=[O:9].CO.O>ClCCl>[F:5][C:6]1[C:13]([F:14])=[CH:12][CH:11]=[C:10]([OH:15])[C:7]=1[CH:8]=[O:9]

Participants

6

Reactant 4

HCID 887MethanolHCID 962WaterHCID 25134Boron tribromideHCID 27741122,3-Difluoro-6-methoxybenzaldehyde

Product 1

HCID 212210312,3-Difluoro-6-hydroxybenzaldehyde

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of boron tribromide in dichloromethane (1.0 M; 197.4 ml) was added to a solution of 2,3-difluoro-6-methoxybenzaldehyde (10.4 g; prepared in a similar manner to that described above) in dichloromethane (100 ml) under nitrogen stirring below -20° C. The resulting solution was allowed to warm to ambient temperature overnight, then methanol (200 ml) followed by water (100 ml) were added, and the mixture heated at 40° C. for 2 hours. The aqueous layer was separated and extracted with dichloromethane (2×300 ml). The combined organic solutions were extracted with aqueous sodium hydroxide solution (1 M; 3×400 ml) and the combined extracts acidified with concentrated hydrochloric acid, then extracted with ethyl acetate (3×300 ml). These combined extracts were dried over magnesium sulphate and the solvent removed in vacuo to give 2,3-difluoro-6-hydroxybenzaldehyde (8.12 g) as a solid.

Workup

  1. customprepared in a similar manner to that
  2. custombelow -20° C
  3. additionwere added
  4. temperaturethe mixture heated at 40° C. for 2 hours
  5. customThe aqueous layer was separated
  6. extractionextracted with dichloromethane (2×300 ml)
  7. extractionThe combined organic solutions were extracted with aqueous sodium hydroxide solution (1 M; 3×400 ml)
  8. extractionextracted with ethyl acetate (3×300 ml)
  9. dry with materialThese combined extracts were dried over magnesium sulphate
  10. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-72c51c8f4f0c4f0d81d1855b1d11826b
Source dataset
uspto-grants-1999_08
Patent number
US05935973

Reaction notes

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