Triphenylphosphine → 4-(Ethoxycarbonylmethoxy)benzyltriphenylphosphonium bromide

HRID 1459435Notes

Reaction equation

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

Participants

Conditions

Temperature: 50 °C

Procedure

To a 100 mL round bottomed flask with a stirring bar and a reflux condenser topped with an argon inlet was added ethyl 2-(4-bromomethylphenoxy)acetate 35-5 (2.73 g, 10 mmol), triphenylphosphine (2.62 g, 10 mmol) and dry benzene (50 mL). This solution was warmed to 50° C. for 20 h. The mixture was cooled to room temperature and the product was collected by filtration. The white solid was washed with a little benzene and dried in vacuo to give 4-(ethoxycarbonylmethoxy)benzyltriphenyl-phosphonium bromide 35-6 as a white, crystalline solid (4.79 g, 89%). 1H NMR (CDCl3): δ 1.28 (t, J=7 Hz, 3H), 4.27 (q, J=7 Hz, 2H), 4.53 (s, 2H), 5.38 (d, J=14 Hz, 2H), 6.66 (d, J=9 Hz, 2H), 7.06 (d, J=9 Hz, 2H), 7.62 (m, 6H), 7.76 (m, 9H).

Workup

customTo a 100 mL round bottomed flask with a stirring bar and a reflux condenser topped with an argon inlet
temperatureThe mixture was cooled to room temperature
filtrationthe product was collected by filtration
washThe white solid was washed with a little benzene
customdried in vacuo

Sources & evidence

ORD record: ord-ed71e204d0264b0892db61ac4295261c
Source dataset: uspto-grants-1998_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05854245

Reaction notes

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