Triphenylphosphine → (7-Carboxyheptyl)triphenylphosphonium bromide

HRID 1651213Notes

Reaction equation

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

Participants

Reactant 2

HCID 11776Triphenylphosphine

HCID 5482758-Bromooctanoic acid

Product 1

HCID 11317723(7-Carboxyheptyl)triphenylphosphonium bromideYield 88.5%

Procedure

Triphenylphosphine (26.3 g) and 8-bromooctanoic acid (21.3 g) were reacted as in Example 82. The crude salt was crystallized from a mixture of ethanol (100 mL), chloroform (200 mL) and ether (500 mL) to give 41 g of (7-carboxyheptyl) triphenylphosphonium bromide, mp 121°-123° C. Anal. Calculated for C26H30BrO2P: C, 64.33; H, 6.23; Br, 16.46. Found: C, 63.97; H, 6.23; Br, 16.07.

Workup

customThe crude salt was crystallized from a mixture of ethanol (100 mL), chloroform (200 mL) and ether (500 mL)

Sources & evidence

ORD record: ord-17c21f1d935d4bb4b31092deac3f8a2e
Source dataset: uspto-grants-1990_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04927838

Reaction notes

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