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Dimethylformamide → Methyl 7-(trifluoromethyl)-1-benzothiophene-2-carboxylate

HRID 2271306
Notes
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Reaction equation

HRID 2271306 reaction equation
F[C:2]1[C:9]([C:10]([F:13])([F:12])[F:11])=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]=O.[C:14]([O:18][CH3:19])(=[O:17])[CH2:15][SH:16].C(=O)([O-])[O-].[K+].[K+].CN(C=O)C>O>[F:11][C:10]([F:13])([F:12])[C:9]1[C:2]2[S:16][C:15]([C:14]([O:18][CH3:19])=[O:17])=[CH:4][C:3]=2[CH:6]=[CH:7][CH:8]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 16907Methyl ThioglycolateHCID 5179782-Fluoro-3-(trifluoromethyl)benzaldehyde

Product 1

HCID 18526203Methyl 7-(trifluoromethyl)-1-benzothiophene-2-carboxylateYield 89.9%

Reagents, catalysts & solvents 1

HCID 962
Water
Solvent

Conditions

Temperature
60 °C

Procedure

A mixture of 1.10 g of 2-fluoro-3-(trifluoromethyl)benzaldehyde, 663 mg of methyl thioglycolate, 1.03 g of potassium carbonate and 15 ml of DMF was stirred at 60° C. for 2 hours. The reaction mixture was cooled to room temperature. To the reaction mixture was added water, and then extracted with tert-butyl methyl ether 3 times. The combined organic layer was washed with water, followed by saturated aqueous sodium chloride solution. The mixture was dried over magnesium sulfate; and then concentrated under reduced pressure to obtain 1.34 g of methyl 7-(trifluoromethyl)benzo[b]thiophene-2-carboxylate (the present compound 4).

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. extractionextracted with tert-butyl methyl ether 3 times
  3. washThe combined organic layer was washed with water
  4. dry with materialThe mixture was dried over magnesium sulfate
  5. concentrationand then concentrated under reduced pressure

Sources & evidence

ORD record
ord-02fd34350e7942eba74e894e4aac31d7
Source dataset
uspto-grants-2015_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09119396B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes