Water → 2-Fluoro-6-methoxybenzaldehyde

HRID 1584873Notes

Reaction equation

HRID 1584873 reaction equation
C([Li])CCC.[F:6][C:7]1[CH:8]=[C:9]([O:13][CH3:14])[CH:10]=[CH:11][CH:12]=1.CN(C)[CH:17]=[O:18].O>O1CCCC1>[F:6][C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([O:13][CH3:14])[C:8]=1[CH:17]=[O:18]

Participants

6

Reactant 4

HCID 962WaterHCID 6228DimethylformamideHCID 99753-FluoroanisoleHCID 178418339Butyllithium

Product 1

HCID 27373572-Fluoro-6-methoxybenzaldehyde

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of butyllithium in hexanes (2.5 M; 15.9 ml) was added to a stirring solution of 3-fluoroanisole (5.0 g) in dry tetrahydrofuran (100 ml) at -78° C. and the mixture stirred at that temperature for 30 min. Dry dimethylformamide (3.1 ml) was added and the mixture stirred and allowed to warm to ambient temperature during one hour. Water (150 ml) was added and the mixture extracted with ethyl acetate (3×100 ml). The combined extracts were washed with brine (100 ml), dried over magnesium sulphate, and the solvent removed in vacuo. Distillation of the residue under reduced pressure gave 2-fluoro-6-methoxybenzaldehyde (4.6 g) as an oil b.p. 120° C. at 10.66 mbar.

Workup

  1. stirringthe mixture stirred
  2. extractionthe mixture extracted with ethyl acetate (3×100 ml)
  3. washThe combined extracts were washed with brine (100 ml)
  4. dry with materialdried over magnesium sulphate
  5. customthe solvent removed in vacuo
  6. distillationDistillation of the residue under reduced pressure

Sources & evidence

ORD record
ord-a183c6f4afa74e67958dccf7d4b674a3
Source dataset
uspto-grants-1999_08
Patent number
US05935973

Reaction notes

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