Water → 3-Bromo-6-hydroxy-2-methylbenzaldehyde

HRID 2036044Notes

Reaction equation

HRID 2036044 reaction equation
B(Br)(Br)Br.[Br:5][C:6]1[C:7]([CH3:16])=[C:8]([C:11]([O:14]C)=[CH:12][CH:13]=1)[CH:9]=[O:10].O.C(OCC)(=O)C.CCCCCC>ClCCl>[Br:5][C:6]1[C:7]([CH3:16])=[C:8]([C:11]([OH:14])=[CH:12][CH:13]=1)[CH:9]=[O:10]

Participants

6

Reactant 4

HCID 962WaterHCID 25134Boron tribromideHCID 112416683-Bromo-6-methoxy-2-methylbenzaldehydeHCID 21226206Ethyl acetate hexane

Product 1

HCID 156998303-Bromo-6-hydroxy-2-methylbenzaldehydeYield 73.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of boron tribromide (12.62 ml, 0.087 mol) in dichloromethane (50 ml) was added to a stirred solution of 3-Bromo-6-methoxy-2-methyl-benzaldehyde (20.0 g, 0.087 mol) in dichloromethane (350 ml) under nitrogen at 0° C. The reaction mixture was stirred for 1.5 hours. Water (400 ml) was added cautiously and the mixture was stirred for 15 min. The organic layer was washed with sodium bicarbonate solution (200 ml), water (200 ml) and brine (200 ml). The organic layer was dried over sodium sulfate and concentrated under reduced pressure to give the crude product as orange brown solid. Column chromatography using 3/97 ethyl acetate/hexane yielded 3-Bromo-6-hydroxy-2-methyl-benzaldehyde (13.82 g, 73.6%).

Workup

  1. stirringthe mixture was stirred for 15 min
  2. washThe organic layer was washed with sodium bicarbonate solution (200 ml), water (200 ml) and brine (200 ml)
  3. dry with materialThe organic layer was dried over sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customto give the crude product as orange brown solid

Sources & evidence

ORD record
ord-7483d5851a8f4b53802bad11263461c0
Source dataset
uspto-grants-2013_11
Patent number
US08575161B2

Reaction notes

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