1,2-Difluorobenzene → 1-(4'-n-Pentyl-2,3-difluorobiphenyl-4-yl)-2-(4-propylphenyl)-ethane

HRID 1590547Notes

Reaction equation

[Li]CCCC.[CH2:6]([C:11]1[CH:16]=[CH:15][C:14]([C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([F:23])[C:18]=2[F:24])=[CH:13][CH:12]=1)[CH2:7][CH2:8][CH2:9][CH3:10].FC1C=CC=CC=1F.C(C1CCC(=O)CC1)CCCC.[CH2:45]([C:48]1[CH:53]=[CH:52][C:51]([CH2:54][CH2:55]I)=[CH:50][CH:49]=1)[CH2:46][CH3:47]>CCCCCC.C1COCC1.CN1C(=O)N(C)CCC1>[CH2:6]([C:11]1[CH:16]=[CH:15][C:14]([C:17]2[CH:22]=[CH:21][C:20]([CH2:55][CH2:54][C:51]3[CH:50]=[CH:49][C:48]([CH2:45][CH2:46][CH3:47])=[CH:53][CH:52]=3)=[C:19]([F:23])[C:18]=2[F:24])=[CH:13][CH:12]=1)[CH2:7][CH2:8][CH2:9][CH3:10]

Participants

Conditions

Temperature: -40 °C

Procedure

0.15 mol of a solution of n-BuLi in hexane is added dropwise to a mixture of 0.1 mol of 4'-n-pentyl-2,3-difluorobiphenyl (prepared from 1,2-difluorobenzene and 4-pentylcyclohexanone analogously to Example 3), in 250 ml of THF and 0.1 mol of potassium tert. butylate at -90° C. After stirring for 10 minutes at -85° C. a solution of 0.1 mol of 1-(4-propylphenyl)-2-iodoethane in 50 ml of THF and 2 ml of DMPU is added dropwise. After warming up to -40° C. and customary work-up 1-(4'-n-pentyl-2,3-difluorobiphenyl-4-yl)-2-(4-propylphenyl)-ethane is obtained.

Workup

customat -90° C
additionis added dropwise

Sources & evidence

ORD record: ord-b00ad94cdf4d4a928433a283bac12db9
Source dataset: uspto-grants-1993_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05204019

Reaction notes

Loading…