Water → 6-Fluorosalicylaldehyde

HRID 1584874Notes

Reaction equation

HRID 1584874 reaction equation
B(Br)(Br)Br.[F:5][C:6]1[CH:13]=[CH:12][CH:11]=[C:10]([O:14]C)[C:7]=1[CH:8]=[O:9].O>ClCCl>[F:5][C:6]1[CH:13]=[CH:12][CH:11]=[C:10]([OH:14])[C:7]=1[CH:8]=[O:9]

Participants

5

Reactant 3

HCID 962WaterHCID 25134Boron tribromideHCID 27373572-Fluoro-6-methoxybenzaldehyde

Product 1

HCID 27373276-FluorosalicylaldehydeYield 47.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of boron tribromide in dichloromethane (1M; 20.15 ml) was added dropwise to a stirring solution of 2-fluoro-6-methoxybenzaldehyde (4.66 g, prepared as described above) in dichloromethane (40 ml) at -78° C. The mixture was allowed to warm to ambient temperature then water (150 ml) was added and the mixture extracted with dichloromethane (3×100 ml). The combined extracts were washed with water (100 ml) then brine (100 ml) and the solvent evaporated. Distillation of the residue at reduced pressure gave 2-fluoro-6-hydroxybenzaldehyde (2.0 g), contaminated with 7% of the starting methoxy compound, as an oil b.p. 60° C. at 4.66 mbar, which was used without further purification.

Workup

  1. extractionthe mixture extracted with dichloromethane (3×100 ml)
  2. washThe combined extracts were washed with water (100 ml)
  3. custombrine (100 ml) and the solvent evaporated
  4. distillationDistillation of the residue at reduced pressure

Sources & evidence

ORD record
ord-7ffcca530d2140349b0002286f79141d
Source dataset
uspto-grants-1999_08
Patent number
US05935973

Reaction notes

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