o-Toluenesulfonyl chloride → HCID 67878066, compound

HRID 2253723Notes

Reaction equation

HRID 2253723 reaction equation
[F:1][C:2]1[C:7]([F:8])=[C:6]([OH:9])[CH:5]=[CH:4][C:3]=1[C:10]1[CH:15]=[CH:14][C:13]([CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH2:12][CH:11]=1.C(=O)([O-])[O-].[K+].[K+].C1(C)C=CC(S(O[CH2:43][C@@H:44]([F:51])[CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH3:50])(=O)=O)=CC=1.F[C@@H](CCCCCC)CO.C1(C)C(S(Cl)(=O)=O)=CC=CC=1>CN(C)C=O.N1C=CC=CC=1>[F:1][C:2]1[C:7]([F:8])=[C:6]([O:9][CH2:43][CH:44]([F:51])[CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH3:50])[CH:5]=[CH:4][C:3]=1[C:10]1[CH:11]=[CH:12][C@@:13]([CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])([C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH2:14][CH:15]=1

Participants

8

Reactant 5

HCID 8623o-Toluenesulfonyl chlorideHCID 11430Potassium CarbonateHCID 11137325(S)-2-fluorooctane-1-olHCID 14297707HCID 14297707, compoundHCID 67878061HCID 67878061, compound

Product 1

HCID 67878066HCID 67878066, compound

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6228DimethylformamideSolvent

Procedure

0.02 mol of 2,3-difluoro-4-hydroxy-4'-pentyl-p-terphenyl, 0.02 mol of potassium carbonate and 0.2 mol of (S)-2-fluorooctyl p-toluenesulfonate (prepared from (S)-2-fluorooctan-1-ol and toluenesulfonyl chloride in the presence of pyridine) are stirred at 60° for 15 hours in 25 ml of dimethylformamide. The undissolved salts are filtered off with suction, and water is added to the filtrate. Extractive work-up and subsequent column chromatography give the pure (S)-2,3-difluoro-4-(2-fluorooctyloxy)-4'-pentyl-p-terphenyl.

Workup

  1. filtrationThe undissolved salts are filtered off with suction, and water
  2. additionis added to the filtrate

Sources & evidence

ORD record
ord-320fd4f635f94ba6b1ceb13d48501c39
Source dataset
uspto-grants-1993_08
Patent number
US05232624

Reaction notes

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