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

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. The resulting mixture was washed with 1×50 mL of brine. The mixture was dried over sodium sulfate and concentrated under vacuum. This resulted in 4.4 g (64%) of 3-(acetylthiomethyl)benzoic acid as a brown solid.

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 materialThe mixture was dried over sodium sulfate
7. concentrationconcentrated under vacuum
8. customThis resulted in 4.4 g (64%) of 3-(acetylthiomethyl)benzoic acid as a brown solid

ORD record

ord-e3b795d7510c49f59fb2e43241e3f0a3

Source dataset

uspto-grants-2014_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08916569B2