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

HRID 2406060Notes

Reaction equation

HRID 2406060 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](=[S:15])([O-:14])[CH3:13].[K+]>C(O)C>[C:12]([S:15][CH2:2][C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][CH:11]=1)[C:6]([OH:8])=[O:7])(=[O:14])[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 ethanethioate (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, 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. washwashed 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-c313e60159924ce4a6332de878e7ca8c
Source dataset
uspto-grants-2014_08
Patent number
US08809339B2

Reaction notes

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