Water → 6-Fluoro-2-hydroxy-3-methoxybenzaldehyde

HRID 751554Notes

Reaction equation

HRID 751554 reaction equation
B(Cl)(Cl)Cl.[F:5][C:6]1[C:11]([CH:12]=[O:13])=[C:10]([O:14]C)[C:9]([O:16][CH3:17])=[CH:8][CH:7]=1.O>ClCCl>[F:5][C:6]1[C:11]([CH:12]=[O:13])=[C:10]([OH:14])[C:9]([O:16][CH3:17])=[CH:8][CH:7]=1

Participants

5

Reactant 3

HCID 962WaterHCID 25135Boron TrichlorideHCID 107261486-Fluoro-2,3-dimethoxybenzaldehyde

Product 1

HCID 224828186-Fluoro-2-hydroxy-3-methoxybenzaldehydeYield 95.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

1M boron trichloride in dichloromethane (25 ml; 25 mmol) was added to a solution of 6-fluoro-2,3-dimethoxy-benzaldehyde [Cantrell, Amanda S.; Engelhardt, Per; Hoegberg, Marita; Jaskunas, S. Richard; Johansson, Nils Gunnar; et al.; J.Med.Chem.; 39; 21; 1996; 4261-4274] (4.26 g; 23 mmol) in dichloromethane (30 ml) keeping the reaction temperature at −70 C. The reaction mixture stirred at room temperature overnight and hydrolyzed with water. The organic phase was separated, washed with water and evaporated in vacuo. The residue was chromatographed (silica gel, EA:Hex, 5:1) to give 3.72 g (94%) of 6-fluoro-2-hydroxy-3-methoxy-benzaldehyde as yellow crystals.

Workup

  1. customThe organic phase was separated
  2. washwashed with water
  3. customevaporated in vacuo
  4. customThe residue was chromatographed (silica gel, EA:Hex, 5:1)

Sources & evidence

ORD record
ord-a19a8a734c5445749e09d85bfc25132d
Source dataset
uspto-grants-2008_07
Patent number
US07405310B2

Reaction notes

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