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

HRID 1255720Notes

Reaction equation

HRID 1255720 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-c9d24f7be90b44849ca4a95d4197e077
Source dataset
uspto-grants-2013_06
Patent number
US08461135B2

Reaction notes

Loading…