Triphenylphosphine → 4-Carboxyphenethyltriphenylphosphonium bromide

HRID 642793Notes

Reaction equation

HRID 642793 reaction equation
[Br:1][CH2:2][CH2:3][C:4]1[CH:12]=[CH:11][C:7]([C:8]([OH:10])=[O:9])=[CH:6][CH:5]=1.[C:13]1([P:19]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>C1(C)C=CC=C(C)C=1>[Br-:1].[C:8]([C:7]1[CH:11]=[CH:12][C:4]([CH2:3][CH2:2][P+:19]([C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=2)=[CH:5][CH:6]=1)([OH:10])=[O:9]

Participants

4

Reactant 2

HCID 11776TriphenylphosphineHCID 1040684-(2-Bromoethyl)benzoic acid

Product 1

HCID 226755274-Carboxyphenethyltriphenylphosphonium bromideYield 82.1%

Reagents, catalysts & solvents 1

HCID 7929M-XyleneSolvent

Procedure

p-Bromoethylbenzoic acid (15 mmol, 3.45 g) and triphenylphosphine (16.5 mmol, 4.32 g) were refluxed in 100 ml m-xylene for 9 h (oil bath temperature 150° C.). The mixture was then cooled down, the solid formed was filtered, washed with m-xylene (2×20 ml), hexanes (2×20 ml), and air-dried to give 6.05 g (82%) of beige crystals. Recrystallization from MeOH—CHCl3-hexanes (˜1:3:5) afforded 2.8 g (38%) of pure off-white crystals of 4-carboxyphenethyl(triphenyl)phosphonium bromide. 1H NMR (400 MHz, CDCl3) δ 7.74 (d, 2H, 8.4 Hz, H2, H6 Ar), 7.68 (m, 3H, Ph3P), 7.55 (m, 12H, Ph3P), 7.09 (d, 2H, 8.4 Hz, H3, H5 Ar), 3.48 (m, 2H, CH2—P), 2.86 (m, 2H, CH2—Ar)

Workup

  1. temperatureThe mixture was then cooled down
  2. customthe solid formed
  3. filtrationwas filtered
  4. washwashed with m-xylene (2×20 ml), hexanes (2×20 ml)
  5. customair-dried

Sources & evidence

ORD record
ord-ded09d21094d42cc9b4f0d12fe20e94c
Source dataset
uspto-grants-2010_04
Patent number
US07696243B2

Reaction notes

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