Methanol → HCID 70855549, compound

HRID 591038Notes

Reaction equation

HRID 591038 reaction equation
[Br:1][C:2]1[C:3]2[C:15]([CH3:16])=[CH:14][CH:13]=[CH:12][C:4]=2[S:5][C:6]=1[CH:7]([OH:11])[C:8]([OH:10])=[O:9].S(=O)(=O)(O)O.[CH3:22]O>>[Br:1][C:2]1[C:3]2[C:15]([CH3:16])=[CH:14][CH:13]=[CH:12][C:4]=2[S:5][C:6]=1[CH:7]([OH:11])[C:8]([O:10][CH3:22])=[O:9]

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 70855548HCID 70855548, compound

Product 1

HCID 70855549HCID 70855549, compoundYield 88%

Procedure

A solution of (3-bromo-4-methyl-benzo[b]thiophen-2-yl)-hydroxy-acetic acid (23g) (270 mg, 0.9 mmol) and sulfuric acid (500 μL) in methanol (5 mL) was refluxed for 1 hour. The reaction mixture was then concentrated and the residue was diluted with ethyl acetate (20 mL). The organic layer was washed with water (2×20 mL), a saturated aqueous solution of sodium bicarbonate (20 mL), brine (20 mL), dried over sodium sulfate, filtered and evaporated under reduced pressure to afford the desired product (23h) as a orange solid (250 mg, 0.79 mmol, 88%) without further purification.

Workup

  1. concentrationThe reaction mixture was then concentrated
  2. additionthe residue was diluted with ethyl acetate (20 mL)
  3. washThe organic layer was washed with water (2×20 mL)
  4. dry with materiala saturated aqueous solution of sodium bicarbonate (20 mL), brine (20 mL), dried over sodium sulfate
  5. filtrationfiltered
  6. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-00c68dd7353c42e99ceb21b50f9b1437
Source dataset
uspto-grants-2016_01
Patent number
US09238026B2

Reaction notes

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