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

HRID 2182028Notes

Reaction equation

HRID 2182028 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-b8b9c5340f49489b9843d42ecb27db58
Source dataset
uspto-grants-2005_05
Patent number
US06894177B2

Reaction notes

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