Methyl Bromide → Methyl tris(p-t-amylphenyl)phosphonium Bromide

HRID 444432Notes

Reaction equation

HRID 444432 reaction equation
[C:1]([C:6]1[CH:11]=[CH:10][C:9]([P:12]([C:24]2[CH:29]=[CH:28][C:27]([C:30]([CH2:33][CH3:34])([CH3:32])[CH3:31])=[CH:26][CH:25]=2)[C:13]2[CH:18]=[CH:17][C:16]([C:19]([CH2:22][CH3:23])([CH3:21])[CH3:20])=[CH:15][CH:14]=2)=[CH:8][CH:7]=1)([CH2:4][CH3:5])([CH3:3])[CH3:2].[CH3:35][Br:36]>C1C=CC=CC=1>[Br-:36].[CH3:35][P+:12]([C:13]1[CH:18]=[CH:17][C:16]([C:19]([CH2:22][CH3:23])([CH3:21])[CH3:20])=[CH:15][CH:14]=1)([C:24]1[CH:29]=[CH:28][C:27]([C:30]([CH2:33][CH3:34])([CH3:31])[CH3:32])=[CH:26][CH:25]=1)[C:9]1[CH:10]=[CH:11][C:6]([C:1]([CH2:4][CH3:5])([CH3:2])[CH3:3])=[CH:7][CH:8]=1

Participants

4

Reactant 2

HCID 6323Methyl BromideHCID 12900990Tris(p-t-amylphenyl)phosphine

Product 1

HCID 23463778Methyl tris(p-t-amylphenyl)phosphonium BromideYield 97%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A mixture containing 28.3 g (0.06 mole) of tris(p-t-amylphenyl)phosphine, 28.5 g (0.3 mole) of methyl bromide and 200 cc of benzene was prepared and stored at ambient temperature for 24 hours. The solvent was then removed under reduced pressure and the solid residue was stirred together with a quantity of diethyl ether for one hour. The recovered solid material weighed 33 g (97% yield) after drying and was found to contain 71.3% carbon, 8.44% hydrogen, 5.15% phosphorus and 14.0% bromine. The calculated values for the expected compound are 72.0% carbon, 8.47% hydrogen, 5.47% phosphorus and 14.1% bromine.

Workup

  1. customwas prepared
  2. customThe solvent was then removed under reduced pressure
  3. customafter drying

Sources & evidence

ORD record
ord-be7c1c2ec12744d7918fdaef5340193e
Source dataset
uspto-grants-1981_04
Patent number
US04264593

Reaction notes

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