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

HRID 2036043Notes

Reaction equation

HRID 2036043 reaction equation
[CH3:1][O:2][C:3]1[CH:10]=[CH:9][CH:8]=[C:7]([CH3:11])[C:4]=1[CH:5]=[O:6].[Br:12]Br.O>C(Cl)(Cl)(Cl)Cl.[Fe]>[Br:12][C:8]1[C:7]([CH3:11])=[C:4]([C:3]([O:2][CH3:1])=[CH:10][CH:9]=1)[CH:5]=[O:6]

Participants

6

Reactant 3

HCID 962WaterHCID 24408BromineHCID 6402382-Methoxy-6-methylbenzaldehyde

Product 1

HCID 112416683-Bromo-6-methoxy-2-methylbenzaldehydeYield 92.5%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 5943Carbon TetrachlorideSolvent

Procedure

2-Methoxy-6-methylbenzaldehyde (7.32 g, 0.049 mol) in carbon tetrachloride (183 ml) was cooled to −10° C., and iron powder (150 mg, 0.002 mol) was added to it. Bromine (3.0 ml, 0.058 mol) was added over a period of 10 minutes. The mixture was stirred for 1 hour and then poured into water (225 ml). The organic layer was washed with sodium thiosulfate solution (2×50 ml), water (50 ml) and brine solution (50 ml). The organic layer was dried over sodium sulfate and concentrated under reduced pressure to give 3-Bromo-6-methoxy-2-methyl-benzaldehyde (10.32 g, 92.5%).

Workup

  1. washThe organic layer was washed with sodium thiosulfate solution (2×50 ml), water (50 ml) and brine solution (50 ml)
  2. dry with materialThe organic layer was dried over sodium sulfate
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-a38af56571ea49bbb3b5c6589115ee21
Source dataset
uspto-grants-2013_11
Patent number
US08575161B2

Reaction notes

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