Acetic Acid → HCID 21915266, compound

HRID 2117926Notes

Reaction equation

HRID 2117926 reaction equation
[CH3:1][S:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][C:10]([C:12]2[CH:21]=[CH:20][C:15]([C:16]([O:18][CH3:19])=[O:17])=[CH:14][CH:13]=2)=[O:11])=[CH:5][CH:4]=1.C(O)(=O)C.C1C=C[NH+]=CC=1.[Br:32][Br-]Br.O>ClCCl>[Br:32][CH:9]([C:6]1[CH:5]=[CH:4][C:3]([S:2][CH3:1])=[CH:8][CH:7]=1)[C:10]([C:12]1[CH:13]=[CH:14][C:15]([C:16]([O:18][CH3:19])=[O:17])=[CH:20][CH:21]=1)=[O:11]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 962WaterHCID 15390784HCID 15390784, compound

Product 1

HCID 21915266HCID 21915266, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of methyl 4-{[4-(methylthio)phenyl]acetyl}benzoate (5 g) in dichloromethane (250 ml) were added acetic acid (0.65 ml) and pyridinium bromide perbromide (6.51 g) at 0° C., and the mixture was stirred for 1 h at the same temperarure. The reaction mixture was poured into water (250 ml) and extracted with ethyl acetate (250 ml). The organic layer was washed with water and brine, dried over magnesium sulfate and evapolated. The residue was washed with diisopropylethyl ether and collected by filtration to give methyl 4-{2-bromo[4-(methylthio)phenyl]acetyl}benzoate as an off-white solid.

Workup

  1. extractionextracted with ethyl acetate (250 ml)
  2. washThe organic layer was washed with water and brine
  3. dry with materialdried over magnesium sulfate
  4. washThe residue was washed with diisopropylethyl ether
  5. filtrationcollected by filtration

Sources & evidence

ORD record
ord-cc386f520ff344d18f73c65922c8745d
Source dataset
uspto-grants-2008_10
Patent number
US07442715B2

Reaction notes

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