Diethyl Ether → (2-Carboxyethyl)triphenylphosphonium bromide

HRID 13687

Reaction equation

HRID 13687 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][C:23]([OH:25])=[O:24].CCOCC>C(#N)C>[Br-:20].[C: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:25])=[O:24]

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 115533-Bromopropionic acidHCID 11776Triphenylphosphine

Product 1

HCID 2733850(2-Carboxyethyl)triphenylphosphonium bromideYield 68.5%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Reflux a solution of triphenylphosphine (91.3 g, 348 mmol, 1.05 equivalents) and 3-bromopropionic acid (50.7 g, 331 mmol) in acetonitrile (250 ml) for three hours, allow to sit at room temperature overnight. Add ether (400 ml) and cool in the freezer for two hours. Filter solids, rinse with ether, and dry solids under high vacuum to obtain the title compound (94.1 g, 68%). NMR (400 MHz, CDCl3): δ 3.15 (m, 2H), 3.73 (m, 2H), 7.69-7.83 (m, 15H).

Workup

  1. filtrationFilter solids
  2. washrinse with ether
  3. customdry solids under high vacuum

Sources & evidence

ORD record
ord-060003a7a2704584a930000b029c00b0
Source dataset
uspto-grants-2010_06
Patent number
US07728150B2

Linked notes

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