Triphenylphosphine → HCID 178444282, compound

HRID 1380782Notes

Reaction equation

[Br:1][CH2:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:14]=[CH:13][C:12]([C@H:15]3[CH2:20][CH2:19][C@H:18]([CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])[CH2:17][CH2:16]3)=[CH:11][CH:10]=2)=[CH:5][CH:4]=1.[C:26]1([P:32]([C:39]2[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=2)[C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1>CC1C=CC=CC=1C>[Br-:1].[CH2:21]([C@H:18]1[CH2:17][CH2:16][C@H:15]([C:12]2[CH:11]=[CH:10][C:9]([C:6]3[CH:7]=[CH:8][C:3]([CH2:2][P+:32]([C:26]4[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=4)([C:33]4[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=4)[C:39]4[CH:40]=[CH:41][CH:42]=[CH:43][CH:44]=4)=[CH:4][CH:5]=3)=[CH:14][CH:13]=2)[CH2:20][CH2:19]1)[CH2:22][CH2:23][CH2:24][CH3:25]

Participants

Conditions

Temperature: 160 °C

Procedure

A mixture of 2.63 g of 4-(bromomethyl)-4'-(trans-4-pentylcyclohexyl)biphenyl and 2.2 g of triphenylphosphine in 150 ml of o-xylene was heated to reflux (bath temperature 160° C.) for 15 hours in a sulphonation flask while gassing with argon. After cooling, the white precipitate formed was filtered off, washed several times with benzene and dried in a high vacuum (0.1 mmHg) at 80° C. for 1 hour. There were obtained 3.48 g (80%) of [[4'-(trans-4-pentylcyclohexyl)-4-biphenylyl]methyl]triphenylphosphonium bromide as a white powder (m.p. 263°-265° C.) which was used in the following Wittig reaction without further purification.

Workup

temperaturewas heated
temperatureAfter cooling
customthe white precipitate formed
filtrationwas filtered off
washwashed several times with benzene
customdried in a high vacuum (0.1 mmHg) at 80° C. for 1 hour

Sources & evidence

ORD record: ord-2453deedf49444f1ad3d932637a0791b
Source dataset: uspto-grants-1986_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04583826

Reaction notes

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