Tributylphosphine → HCID 67008108, compound

HRID 1256940Notes

Reaction equation

HRID 1256940 reaction equation
[C:1]([O:5][C:6](=[O:15])[C:7]1[CH:12]=[CH:11][C:10]([CH2:13][Br:14])=[CH:9][CH:8]=1)([CH3:4])([CH3:3])[CH3:2].[CH2:16]([P:20]([CH2:25][CH2:26][CH2:27][CH3:28])[CH2:21][CH2:22][CH2:23][CH3:24])[CH2:17][CH2:18][CH3:19]>C1(C)C=CC=CC=1>[Br-:14].[C:1]([O:5][C:6]([C:7]1[CH:12]=[CH:11][C:10]([CH2:13][P+:20]([CH2:21][CH2:22][CH2:23][CH3:24])([CH2:25][CH2:26][CH2:27][CH3:28])[CH2:16][CH2:17][CH2:18][CH3:19])=[CH:9][CH:8]=1)=[O:15])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 13831TributylphosphineHCID 11414578Tert-butyl 4-(bromomethyl)benzoate

Product 1

HCID 67008108HCID 67008108, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 4-(bromomethyl)benzoic acid tert-butyl ester (22.1 g) in toluene (440 ml), tri-n-butylphosphine (30.5 ml) was added, and the mixed solution was stirred at 60° C. for 70 min. The reaction solution was removed by evaporation under reduced pressure, and to the resulting crude product, n-hexane was added and stirred. The resulting solid was filtered out to give [4-(tert-butoxycarbonyl)benzyl](tributyl)phosphonium bromide (36.0 g) as a colorless solid.

Workup

  1. customThe reaction solution was removed by evaporation under reduced pressure
  2. additionto the resulting crude product, n-hexane was added
  3. stirringstirred
  4. filtrationThe resulting solid was filtered out

Sources & evidence

ORD record
ord-dec1a20ca8f547f38b9ebad8a1c47e96
Source dataset
uspto-grants-2013_06
Patent number
US08461329B2

Reaction notes

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