Methanol → HCID 86717838, compound

HRID 591030Notes

Reaction equation

HRID 591030 reaction equation
[Br:1][C:2]1[C:3]2[CH:15]=[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.[CH3:21]O>>[Br:1][C:2]1[C:3]2[CH:15]=[CH:14][CH:13]=[CH:12][C:4]=2[S:5][C:6]=1[CH:7]([OH:11])[C:8]([O:10][CH3:21])=[O:9]

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 86717839HCID 86717839, compound

Product 1

HCID 86717838HCID 86717838, compoundYield 91%

Procedure

A solution of (3-bromo-benzo[b]thiophen-2-yl)-hydroxy-acetic acid (21b) (590 mg, 2.05 mmol) and sulfuric acid (500 μL) in methanol (10 mL) was refluxed for 1 hour. The reaction mixture was then concentrated in vacuo and the residue was diluted with ethyl acetate (20 mL). The organic layer was washed with water (2×20 mL), a saturated solution of sodium bicarbonate (20 mL), brine (20 mL), dried over sodium sulfate, filtered and evaporated under reduced pressure to afford the desired ester (21c) as a orange solid (560 mg, 1.86 mmol, 91%) without further purification.

Workup

  1. concentrationThe reaction mixture was then concentrated in vacuo
  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 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-11cf74a44cf44934b3a1a836a463876e
Source dataset
uspto-grants-2016_01
Patent number
US09238026B2

Reaction notes

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