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

HRID 606336Notes

Reaction equation

HRID 606336 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. customat −70° C
  2. customThe organic phase was separated
  3. washwashed with water
  4. customevaporated in vacuo
  5. customThe residue was chromatographed (silica gel, EA:Hex, 5:1)

Sources & evidence

ORD record
ord-7b7de126cb8a426db9700fa85a299413
Source dataset
uspto-grants-2011_03
Patent number
US07915295B2

Reaction notes

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