Reaction #76402

Reaction equation

2′,3′-difluoro-4′-(5,5,6,6,7,7,8,8,8-nonafluoro-octyloxy)-biphenyl-4-carboxylic acid

4-hydroxy benzoic acid (R)-1-trifluoromethyl-heptyl ester

4-Hydroxy Benzoic Acid (R)-1-Trifluoromethyl-heptyl Ester

DMAP

→

2′,3′-difluoro-4′-(5,5,6,6,7,7,8,8,8-nonafluoro-octyloxy)-biphenyl-4-carboxylic acid 4-[(R)-1-trifluoromethyl-heptyloxycarbonyl]-phenyl ester

Yield 65.0%

Solvents

THF

DIC

Conditions

Workup

1. 1
   Otherquenched with water
2. 2
   Extractionextracted with ethyl acetate:hexane(1:1)
3. 3
   Washwashed with brine
4. 4
   Dryingdried over MgSO4
5. 5
   Concentrationconcentrated in vacuo
6. 6
   OtherPurification by chromatography on silica gel (5% EtOAc/hexanes)

Procedure

To a solution of 2′,3′-difluoro-4′-(5,5,6,6,7,7,8,8,8-nonafluoro-octyloxy)-biphenyl-4-carboxylic acid (14 A) (1 equi.), (4-hydroxy benzoic acid (R)-1-trifluoromethyl-heptyl ester (7) (1 equi.), and DMAP (dimethylaminopyridine) (0.1 equi.) in THF (25 mL/mmole), DIC (diisopropyl carbodiimide) (1.2 equi.) was added at room temperature. The reaction mixture was stirred at that temperature for 24 h, quenched with water, extracted with ethyl acetate:hexane(1:1), washed with brine, dried over MgSO4, and concentrated in vacuo. Purification by chromatography on silica gel (5% EtOAc/hexanes) gave 2′,3′-difluoro-4′-(5,5,6,6,7,7,8,8,8-nonafluoro-octyloxy)-biphenyl-4-carboxylic acid 4-[(R)-1-trifluoromethyl-heptyloxycarbonyl]-phenyl ester (15A) as a white solid (65%).

Source