Bromine → HCID 21996470, compound

HRID 1977999Notes

Reaction equation

HRID 1977999 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:5][C:4]=1[CH3:16].COC1C=CC(C=O)=CC=1C.[Br:28]Br>C(Cl)(Cl)Cl>[Br:28][C:8]1[CH:7]=[C:6]([CH2:9][CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12])[CH:5]=[C:4]([CH3:16])[C:3]=1[O:2][CH3:1]

Participants

5

Reactant 3

HCID 24408BromineHCID 1229363-Methyl-4-anisaldehydeHCID 21996524HCID 21996524, compound

Product 1

HCID 21996470HCID 21996470, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a solution of ethyl 3-(4-methoxy-3-methylphenyl)propionate (derived from 10.0 g (66.6 mmol) of 4-methoxy-3-methylbenzaldehyde) in chloroform (200 ml) was added dropwise bromine (10.6 g, 66.6 mmol). The mixture was stirred for 12 hours at room temperature. The reaction mixture was washed with water, an aqueous solution of sodium thiosulfate, which was dried over anhydrous magnesium sulfate, followed by distilling off the solvent under reduced pressure. The residue was purified by means of a silica gel column chromatography (hexane→hexane/ethyl acetate, 9:1) to give 17.0 g (yield 85%; 3 steps) of the above-titled compound as an oily product.

Workup

  1. washThe reaction mixture was washed with water
  2. dry with materialan aqueous solution of sodium thiosulfate, which was dried over anhydrous magnesium sulfate
  3. distillationby distilling off the solvent under reduced pressure
  4. customThe residue was purified by means of a silica gel column chromatography (hexane→hexane/ethyl acetate, 9:1)

Sources & evidence

ORD record
ord-2271ee9462a4420cb56d119cae13660e
Source dataset
uspto-grants-2001_05
Patent number
US06235789B1

Reaction notes

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