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

HRID 23327

Reaction equation

HRID 23327 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-c4f7d550f4084b819d2aa770f40142bf
Source dataset
uspto-grants-2005_02
Patent number
US06852673B2

Linked notes

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