Oxalyl chloride → Benzo[b]thiophene-2-carboxylic acid, 5-(trifluoromethyl)-, ethyl ester

HRID 2271308Notes

Reaction equation

HRID 2271308 reaction equation
[C:1](Cl)(=[O:5])[C:2](Cl)=O.[F:7][C:8]([F:22])([F:21])[C:9]1[CH:20]=[CH:19][C:12]2[S:13][C:14]([C:16](O)=[O:17])=[CH:15][C:11]=2[CH:10]=1>C(O)C>[F:21][C:8]([F:7])([F:22])[C:9]1[CH:20]=[CH:19][C:12]2[S:13][C:14]([C:16]([O:5][CH2:1][CH3:2])=[O:17])=[CH:15][C:11]=2[CH:10]=1

Participants

4

Reactant 2

HCID 65578Oxalyl chlorideHCID 27830435-(Trifluoromethyl)-1-benzothiophene-2-carboxylic acid

Product 1

HCID 70982228Benzo[b]thiophene-2-carboxylic acid, 5-(trifluoromethyl)-, ethyl esterYield 74.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Then, 254 mg of oxalyl chloride was added to a mixture of 400 mg of 5-(trifluoromethyl)benzo[b]thiophene-2-carboxylic acid and 20 ml of ethanol while ice-cooling, and the mixture was stirred for 6 hours under reflux. The reaction mixture was cooled to room temperature, and then concentrated under reduced pressure. To the residue was added chloroform, and then the organic layer was washed with saturated aqueous sodium bicarbonate solution and saturated aqueous sodium chloride solution, dried over magnesium sulfate, and then concentrated under reduced pressure to obtain 330 mg of ethyl 5-(trifluoromethyl)benzo[b]thiophene-2-carboxylate (the present compound 5).

Workup

  1. temperaturecooling
  2. temperatureunder reflux
  3. concentrationconcentrated under reduced pressure
  4. additionTo the residue was added chloroform
  5. washthe organic layer was washed with saturated aqueous sodium bicarbonate solution and saturated aqueous sodium chloride solution
  6. dry with materialdried over magnesium sulfate
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-acfe27147c714dbf9aa70e020235efe9
Source dataset
uspto-grants-2015_09
Patent number
US09119396B2

Reaction notes

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