Triphenylphosphine → (6-(Benzyloxy)-2,3-difluorophenethyl)triphenylphosphonium, iodide salt

HRID 921179Notes

Reaction equation

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

Participants

Conditions

Temperature: 140 °C

Procedure

To a solution of 1-(benzyloxy)-3,4-difluoro-2-(2-iodoethyl)benzene (720 mg, 1.924 mmol) in Xylene (10 mL) was added Ph3P (1514 mg, 5.77 mmol) and the mixture was heated at 140° C. for 16 h. The mixture was cooled to rt (The product solidified). Solids were then filtered off and washed with toluene and ether, dried under high vac to afford (6-(benzyloxy)-2,3-difluorophenethyl)triphenylphosphonium, iodide salt (600 mg, 0.943 mmol, 49.0% yield) as white solid. 1H NMR (500 MHz, CDCl3) δ 7.87-7.77 (m, 3H), 7.77-7.59 (m, 12H), 7.53-7.44 (m, 2H), 7.40-7.33 (m, 3H), 7.02 (q, J=9.3 Hz, 1H), 6.70 (d, J=9.1 Hz, 1H), 5.15 (s, 2H), 3.81-3.69 (m, 2H), 3.10-2.98 (m, 2H). LCMS (M+H)=510.2.

Workup

temperatureThe mixture was cooled to rt (The product
filtrationSolids were then filtered off
washwashed with toluene and ether
customdried under high vac

Sources & evidence

ORD record: ord-b81d50b18db84f3e8632e49230a495f7
Source dataset: uspto-grants-2016_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09273067B2

Reaction notes

Loading…