Triphenylphosphine → (4-(tert-Butyldimethylsilyloxy)-3-ethoxyphenyl)methyltriphenylphosphonium bromide

HRID 718542Notes

Reaction equation

[Br:1][CH2:2][C:3]1[CH:16]=[CH:15][C:6]([O:7][Si:8]([C:11]([CH3:14])([CH3:13])[CH3:12])([CH3:10])[CH3:9])=[C:5]([O:17][CH2:18][CH3:19])[CH:4]=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=CC=CC=1>[Br-:1].[Si:8]([O:7][C:6]1[CH:15]=[CH:16][C:3]([CH2:2][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)=[CH:4][C:5]=1[O:17][CH2:18][CH3:19])([C:11]([CH3:14])([CH3:13])[CH3:12])([CH3:10])[CH3:9]

Participants

Conditions

Temperature: 25 °C

Procedure

To a solution of (4-(bromomethyl)-2-ethoxyphenoxy)(tert-butyl)dimethylsilane (14.5 g, 41.8 mmol, 1.0 equiv.) in toluene (84 mL), PPh3 (11.0 g, 41.8 mmol, 1.0 equiv.) was added. The mixture was stirred at 25° C. for 20 h and concentrated to yield 25.1 g (99%) of (4-(tert-Butyldimethylsilyloxy)-3-ethoxyphenyl)methyltriphenylphosphonium bromide as a white solid.

Workup

concentrationconcentrated

Sources & evidence

ORD record: ord-f4bdd4be2b08456aa3027fa87aae7ae5
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09193935B2

Reaction notes

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