Acetic Acid → HCID 21915266, compound

HRID 1246516Notes

Reaction equation

HRID 1246516 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 temperature. 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-eff65a75d17048af8f43c52ac337edb5
Source dataset
uspto-grants-2006_10
Patent number
US07125901B2

Reaction notes

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