Triphenylphosphine → [4-(Methoxycarbonyl)benzyl](triphenyl)phosphonium bromide

HRID 5052

Reaction equation

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

Participants

Conditions

Temperature: 80 °C

Procedure

To a 2 L 3-neck round bottom flask fitted with a glass stopper, rubber septum, and reflux condenser with a nitrogen inlet tube, was added 64.90 g (283 mmol) methyl 4-bromomethyl benzoate, 81.74 g (311 mmol) triphenylphosphine, and 744 mL toluene. The solution was heated at 80° C. for 5 h. After cooling to room temperature, the reaction vessel was placed in an ice bath. The resulting precipitate was filtered, washed with toluene, and dried in a vacuum oven to afford 126.35 g (89%) (4-carbomethoxy)benzyltriphenylphosphonium bromide as a white solid, mp.=248°-250° C.: 1H NMR (CDCl3, 200 MHz) d 3.86 (s, 3H), 5.70 (d, J=15.3 HZ, 2H), 7.24 (m, 4H), 7.71 (m, 15H).

Workup

customTo a 2 L 3-neck round bottom flask fitted with a glass stopper, rubber septum
temperaturereflux condenser with a nitrogen inlet tube
temperatureAfter cooling to room temperature
customthe reaction vessel was placed in an ice bath
filtrationThe resulting precipitate was filtered
washwashed with toluene
customdried in a vacuum oven

Sources & evidence

ORD record: ord-53a7d6a899654a0bba76c803935dd95c
Source dataset: uspto-grants-1993_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05243021

Linked notes

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