Triphenylphosphine → [7-(4-Methylphenyl)-2,3-dihydro-1-benzooxepin-4-yl]methyltriphenylphosphonium bromide

HRID 1169379Notes

Reaction equation

HRID 1169379 reaction equation
[Br:1][CH2:2][C:3]1[CH2:4][CH2:5][O:6][C:7]2[CH:13]=[CH:12][C:11]([C:14]3[CH:19]=[CH:18][C:17]([CH3:20])=[CH:16][CH:15]=3)=[CH:10][C:8]=2[CH:9]=1.[C:21]1([P:27]([C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>C1(C)C=CC=CC=1>[Br-:1].[CH3:20][C:17]1[CH:18]=[CH:19][C:14]([C:11]2[CH:12]=[CH:13][C:7]3[O:6][CH2:5][CH2:4][C:3]([CH2:2][P+:27]([C:28]4[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=4)([C:34]4[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=4)[C:21]4[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=4)=[CH:9][C:8]=3[CH:10]=2)=[CH:15][CH:16]=1

Participants

4

Reactant 2

HCID 11776TriphenylphosphineHCID 229900924-Bromomethyl-7-(4-methylphenyl)-2,3-dihydro-1-benzooxepine

Product 1

HCID 22990039[7-(4-Methylphenyl)-2,3-dihydro-1-benzooxepin-4-yl]methyltriphenylphosphonium bromideYield 92.9%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Into a solution of 4-bromomethyl-7-(4-methylphenyl)-2,3-dihydro-1-benzooxepine (329 mg) in toluene (10 ml) was added triphenylphosphine (393 mg), and the resulting mixture was refluxed for 2 hours. After gradual cooling, the precipitate was collected by filtration and was washed with toluene. The precipitate was dried under reduced pressure to obtain [7-(4-methylphenyl)-2,3-dihydro-1-benzooxepin-4-yl]methyltriphenylphosphonium bromide (549 mg) as a white powder.

Workup

  1. temperaturethe resulting mixture was refluxed for 2 hours
  2. filtrationAfter gradual cooling, the precipitate was collected by filtration
  3. washwas washed with toluene
  4. customThe precipitate was dried under reduced pressure

Sources & evidence

ORD record
ord-14605cc77a4242e8a573043c582fd540
Source dataset
uspto-grants-2003_09
Patent number
US06627651B1

Reaction notes

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