1,3-Dibromopropane → (3-Bromopropyl)triphenylphosphonium bromide

HRID 484776Notes

Reaction equation

HRID 484776 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]Br>C1(C)C(C)=CC=CC=1>[Br-:20].[Br:20][CH2:21][CH2:22][CH2:23][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

Participants

4

Reactant 2

HCID 80011,3-DibromopropaneHCID 11776Triphenylphosphine

Product 1

HCID 2723862(3-Bromopropyl)triphenylphosphonium bromide

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Conditions

Temperature
130 °C

Procedure

Into a one-liter 3-necked flask equipped with stirrer, condenser, addition funnel, and thermometer there was charged 500 ml xylene and 100 g. triphenylphosphine. There was slowly added 77 grams of 1,3-dibromopropane to the stirred solution at 130° C. After heating for 20 hours at 130° C., the resulting suspension was cooled and filtered to give 131.2 g of (3-bromopropyl)triphenylphosphonium bromide (M.P. 229°-30° C.).

Workup

  1. customInto a one-liter 3-necked flask equipped with stirrer, condenser, addition funnel
  2. customat 130° C
  3. temperaturethe resulting suspension was cooled
  4. filtrationfiltered

Sources & evidence

ORD record
ord-f8b3a2524d004e4fa4027e1f4e9296db
Source dataset
uspto-grants-1985_08
Patent number
US04533722

Reaction notes

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