(3-Benzyloxy-5-trifluoromethylthien-2-yl)-carboxylic acid → 3-Benzyloxy-5-trifluoromethylthiophen

HRID 2229117Notes

Reaction equation

HRID 2229117 reaction equation
[CH2:1]([O:8][C:9]1[CH:13]=[C:12]([C:14]([F:17])([F:16])[F:15])[S:11][C:10]=1C(O)=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>[Cu].N1C2C(=CC=CC=2)C=CC=1>[CH2:1]([O:8][C:9]1[CH:13]=[C:12]([C:14]([F:17])([F:15])[F:16])[S:11][CH:10]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 1

HCID 11426602(3-Benzyloxy-5-trifluoromethylthien-2-yl)-carboxylic acid

Product 1

HCID 111844703-Benzyloxy-5-trifluoromethylthiophenYield 71%

Reagents, catalysts & solvents 2

HCID 23978CopperCatalystHCID 7047QuinolineSolvent

Conditions

Temperature
150 °C

Procedure

A mixture of 5F (14.5 g) and quinoline (50 ml) was treated with copper powder (4.57 g) and heated to 150° C. The reaction mixture is heated for 25 minutes at 150° C. and cooled to room temperature. The mixture was filtered and washed with water. Aqueous quinoline was acidified with 6N HCl (pH=2) and extracted with diethyl ether twice. The combined organic phases were washed with water and dried. The mixture was concentrated and the residue was chromatographed to yield a yellow liquid (8.74 g, 71%).

Workup

  1. temperatureThe reaction mixture is heated for 25 minutes at 150° C.
  2. temperaturecooled to room temperature
  3. filtrationThe mixture was filtered
  4. washwashed with water
  5. extractionextracted with diethyl ether twice
  6. washThe combined organic phases were washed with water
  7. customdried
  8. concentrationThe mixture was concentrated
  9. customthe residue was chromatographed

Sources & evidence

ORD record
ord-1eee47b5239449d7a1de72e196bcfbe4
Source dataset
uspto-grants-2002_07
Patent number
US06420315B1

Reaction notes

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