Triphenylphosphine → (2-Chloro-4-(ethoxycarbonyl)-6-fluorobenzyl)triphenylphosphonium bromide

HRID 83924Notes

Reaction equation

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

Participants

Conditions

Temperature: 90 °C

Procedure

To a solution of ethyl 4-(bromomethyl)-3-chloro-5-fluorobenzoate (531 mg, 1.797 mmol) in toluene (10 mL) was added PPh3 (471 mg, 1.797 mmol). The solution was refluxed at 90° C. overnight. Upon cooling a white precipitate formed. The mixture was diluted with hexanes, filtered and dried under vacuum to yield (2-chloro-4-(ethoxycarbonyl)-6-fluorobenzyl)triphenylphosphonium bromide (0.874 g, 86%) as a white solid. 1H NMR (400 MHz, DMSO-d6) δ 8.05-7.87 (m, 3H), 7.85-7.58 (m, 13H), 7.20 (tt, J=15.1, 7.1 Hz, 1H), 5.21 (d, J=15.0 Hz, 2H), 4.34 (dq, J=14.2, 7.1 Hz, 2H), 1.33 (dt, J=14.2, 7.1 Hz, 3H).

Workup

temperatureUpon cooling a white precipitate
customformed
filtrationfiltered
customdried under vacuum

Sources & evidence

ORD record: ord-d2a1e844a3534dea8948e5d99821c96f
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08846739B2

Reaction notes

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