3-Bromo-α-methylenebenzenepropanoic acid → HCID 10881645, compound

HRID 422902Notes

Reaction equation

HRID 422902 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:11]=[CH:12][CH:13]=1)[CH2:5][C:6](=[CH2:10])[C:7]([OH:9])=[O:8].[C:14]([OH:17])(=[S:16])[CH3:15]>>[C:14]([S:16][CH2:10][CH:6]([CH2:5][C:4]1[CH:11]=[CH:12][CH:13]=[C:2]([Br:1])[CH:3]=1)[C:7]([OH:9])=[O:8])(=[O:17])[CH3:15]

Participants

3

Reactant 2

HCID 179568153-Bromo-α-methylenebenzenepropanoic acidHCID 178418634HCID 178418634, compound

Product 1

HCID 10881645HCID 10881645, compoundYield 95%

Conditions

Temperature
50 °C

Procedure

To a 5 ml pear-shaped flask containing 2-(3-bromobenzyl)acrylic acid (0.44 g, 1.83 mmol) was added thioacetic acid (1 ml, 1.065 g, 13.99 mmol). The mixture was heated at 50° C. for 2.5 hours, after which excess thioacetic acid was removed under reduced pressure. The residue was co-evaporated with toluene twice, then purified via silica gel column chromatography eluting with 0 to 2% MeOH in CH2Cl2, giving 2-(acetylsulfanylmethyl)-3-(3-bromophenyl)propionic acid as a colorless glue, 0.55 g, 95% yield, HPLC purity: 96.9%.

Workup

  1. customafter which excess thioacetic acid was removed under reduced pressure
  2. custompurified via silica gel column chromatography
  3. washeluting with 0 to 2% MeOH in CH2Cl2

Sources & evidence

ORD record
ord-76b92e2a37484caebab2ca4a72008c94
Source dataset
uspto-grants-2012_01
Patent number
US08101665B2

Reaction notes

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