Triphenylphosphine → HCID 131734912, compound

HRID 921152Notes

Reaction equation

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

Participants

Conditions

Temperature: 100 °C

Procedure

To a solution of 2-bromo-4-fluoro-1-(2-iodoethyl)benzene (2.23 g, 6.78 mmol) in toluene (15 ml) was added Ph3P (1.778 g, 6.78 mmol) and the mixture was heated at 100° C. for 16 h. The mixture was cooled to rt, solids were filtered and washed with toluene and ether, dried under high vac to afford (2-bromo-4-fluorophenethyl)triphenylphosphonium, iodide salt (3 g, 5.07 mmol, 74.8% yield) as white solid. 1H NMR (500 MHz, DMSO-d6) δ 8.01-7.87 (m, 9H), 7.85-7.77 (m, 6H), 7.66-7.51 (m, 1H), 7.35-7.24 (m, 1H), 7.20-7.07 (m, 1H), 3.93-3.80 (m, 2H), 3.07-2.86 (m, 2H).

Workup

temperatureThe mixture was cooled to rt
filtrationsolids were filtered
washwashed with toluene and ether
customdried under high vac

Sources & evidence

ORD record: ord-bd434ef8df3b4c8d9230c9cbb3317d64
Source dataset: uspto-grants-2016_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09273067B2

Reaction notes

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