Triphenylphosphine → [(4-Bromophenyl)methyl]triphenylphosphanium bromide

HRID 1967878Notes

Reaction equation

HRID 1967878 reaction equation
[Br:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6]Br)=[CH:4][CH:3]=1.[C:10]1([P:16]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1>CC(C)=O>[Br-:1].[Br:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][P+:16]([C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 11776TriphenylphosphineHCID 685274-Bromobenzyl bromide

Product 1

HCID 2724858[(4-Bromophenyl)methyl]triphenylphosphanium bromideYield 195.2%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

25.2 g (101 mmol) of 4-bromobenzylbromide and 100 mL of acetone were put into a 200 mL conical flask, and then 29.1 g (111 mmol) of triphenylphosphine was added thereto. Thereafter, this mixture was stirred at room temperature for 23 hours to be reacted. After the reaction, a precipitate in the reaction mixture was collected by suction filtration. Then, 50.5 g of objective 4-bromobenzyltriphenylphosphonium bromide was obtained as a white powdered solid in a yield of 98%. Synthetic scheme of 4-bromobenzyltriphenylphosphonium bromide is illustrated below (synthetic scheme a-1).

Workup

  1. customto be reacted
  2. customAfter the reaction
  3. filtrationa precipitate in the reaction mixture was collected by suction filtration

Sources & evidence

ORD record
ord-38e09fe657224124aa92dd6d99139540
Source dataset
uspto-grants-2013_04
Patent number
US08420874B2

Reaction notes

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