Bromine → 2-Bromo-4-fluoro-5-methoxybenzaldehyde

HRID 1471577Notes

Reaction equation

HRID 1471577 reaction equation
[F:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][C:3]=1[O:10][CH3:11].[Br-:12].[K+].BrBr>O>[Br:12][C:8]1[CH:9]=[C:2]([F:1])[C:3]([O:10][CH3:11])=[CH:4][C:5]=1[CH:6]=[O:7]

Participants

5

Reactant 3

HCID 24408Bromine2×HCID 253877Potassium BromideHCID 27373584-Fluoro-3-methoxybenzaldehyde

Product 1

HCID 231579072-Bromo-4-fluoro-5-methoxybenzaldehydeYield 92.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 4-fluoro-3-methoxybenzaldehyde (4.3 g, 27.9 mmol), potassium bromide (16.6 g, 139.5 mmol), bromine (3.6 mL, 69.8 mmol), and water (45 mL) were stirred at room temperature for 24 hours. More bromine (1.43 mL, 27.9 mmol) was added and the reaction was stirred at room temperature overnight. The product precipitated out of solution and was collected via filtration and dried under reduced pressure to give 2-bromo-4-fluoro-5-methoxybenzaldehyde (6.01 g, 92% yield).

Workup

  1. customThe product precipitated out of solution
  2. filtrationwas collected via filtration
  3. customdried under reduced pressure

Sources & evidence

ORD record
ord-8b8869fc1cd0440990fdc2b74201a5e5
Source dataset
uspto-grants-2015_04
Patent number
US09012431B2

Reaction notes

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