Triphenylphosphine → HCID 20274896, compound

HRID 370698Notes

Reaction equation

HRID 370698 reaction equation
[C:1]1([P:7]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Br:20][CH2:21][C:22]1[CH:27]=[CH:26][C:25]([C:28]2[CH:33]=[CH:32][C:31]([CH2:34][CH2:35][CH2:36][CH2:37][CH3:38])=[CH:30][CH:29]=2)=[CH:24][CH:23]=1>C(OCC)(=O)C>[Br-:20].[CH2:34]([C:31]1[CH:32]=[CH:33][C:28]([C:25]2[CH:26]=[CH:27][C:22]([CH2:21][P+:7]([C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)([C:8]3[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=3)[C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=3)=[CH:23][CH:24]=2)=[CH:29][CH:30]=1)[CH2:35][CH2:36][CH2:37][CH3:38]

Participants

4

Reactant 2

HCID 11776TriphenylphosphineHCID 202750004-(Bromomethyl)-4'-pentyl-1,1'-biphenyl

Product 1

HCID 20274896HCID 20274896, compoundYield 56%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

A solution of 11.6 g of triphenylphosphine in 20 ml of ethyl acetate was placed in a sulphonation flask under argon gasification and treated at room temperature within 10 minutes with a solution of 7.5 g of 4-(bromomethyl)-4'-pentylbiphenyl in 15 ml of ethyl acetate. The reaction mixture was subsequently stirred at room temperature for a further 18 hours and then the separated Wittig salt was filtered off, washed with ethyl acetate and dried at 50° C./12 Torr up to constant weight. There were obtained 7.6 g (56%) of (4'-pentyl-4-biphenylyl)methyl-triphenylphosphonium bromide as a colourless powder of melting point 202°-204° C. From the filtrate, concentrated to 50 ml, there could be isolated a further 3.3 g (24%) of the bromide of melting point 202°-204.5° C.

Workup

  1. filtrationthe separated Wittig salt was filtered off
  2. washwashed with ethyl acetate
  3. customdried at 50° C./12 Torr up to constant weight

Sources & evidence

ORD record
ord-a3e856b6ddc4408a949b4bf76d30c57c
Source dataset
uspto-grants-1985_07
Patent number
US04528114

Reaction notes

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