3-(Bromomethyl)benzoic acid → 3-(Acetylthiomethyl)benzoic acid

HRID 926849Notes

Reaction equation

HRID 926849 reaction equation
Br[CH2:2][C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][CH:11]=1)[C:6]([OH:8])=[O:7].[C:12]([O-:15])(=[S:14])[CH3:13].[K+]>C(O)C>[C:12]([S:14][CH2:2][C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][CH:11]=1)[C:6]([OH:8])=[O:7])(=[O:15])[CH3:13]

Participants

4

Reactant 2

HCID 2456503-(Bromomethyl)benzoic acidHCID 23670855Potassium ethanethioate

Product 1

HCID 860892063-(Acetylthiomethyl)benzoic acid

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Into a 250-mL round-bottom flask, was placed a solution of 3-(bromomethyl)benzoic acid (7 g, 32.56 mmol, 1.00 equiv) in ethanol (80 mL), and potassium thioacetate (9.65 g, 84.65 mmol, 2.60 equiv). The resulting solution was stirred overnight at room temperature. The resulting mixture was concentrated under vacuum. The resulting solution was diluted with 80 mL of water and adjusted to pH 3-4 with 10% hydrochloric acid. The resulting solution was extracted with 3×50 mL of ethyl acetate and the organic layers combined. The resulting mixture was washed with 1×50 mL of brine, dried over sodium sulfate, and concentrated under vacuum. This resulted in 4.4 g (64%) of 3-(acetylthiomethyl)benzoic acid as a brown solid.

Workup

  1. customInto a 250-mL round-bottom flask, was placed
  2. concentrationThe resulting mixture was concentrated under vacuum
  3. additionThe resulting solution was diluted with 80 mL of water
  4. extractionThe resulting solution was extracted with 3×50 mL of ethyl acetate
  5. washThe resulting mixture was washed with 1×50 mL of brine
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated under vacuum
  8. customThis resulted in 4.4 g (64%) of 3-(acetylthiomethyl)benzoic acid as a brown solid

Sources & evidence

ORD record
ord-82b2bdc6b6eb4e86ad2589512160c181
Source dataset
uspto-grants-2016_03
Patent number
US09289430B2

Reaction notes

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