2-Aminobenzyl alcohol → (2-Aminobenzyl)triphenylphosphonium bromide

HRID 503366Notes

Reaction equation

HRID 503366 reaction equation
[NH2:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH2:4]O.[BrH:10].[C:11]1([P:17]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1>C(#N)C>[Br-:10].[C:24]1([P+:17]([C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=2)([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH2:4][C:3]2[CH:6]=[CH:7][CH:8]=[CH:9][C:2]=2[NH2:1])[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1

Participants

4

Reactant 2

HCID 214392-Aminobenzyl alcoholHCID 80811Triphenylphosphonium bromide

Product 1

HCID 10961315(2-Aminobenzyl)triphenylphosphonium bromideYield 88.4%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

2-Aminobenzyl alcohol (60.0 g, 0.487 mol) was dissolved in acetonitrile (2.5 L) and brought to reflux. Triphenylphosphine hydrobromide (167 g, 0.487 mol) was added and the mixture was heated at reflux for 3 h. The reaction mixture was concentrated to approximately 500 mL and left at room temperature for 1 h. The precipitate was filtered and washed with cold acetonitrile followed by hexane. The solid was dried overnight at 40° C. under vacuum to give triphenyl(2-aminobenzyl)phosphonium bromide (193 g, 88%).

Workup

  1. temperatureto reflux
  2. temperaturethe mixture was heated
  3. temperatureat reflux for 3 h
  4. concentrationThe reaction mixture was concentrated to approximately 500 mL
  5. filtrationThe precipitate was filtered
  6. washwashed with cold acetonitrile
  7. customThe solid was dried overnight at 40° C. under vacuum

Sources & evidence

ORD record
ord-227b4532e15549158b6b7ee3e1fc86ec
Source dataset
uspto-grants-2010_08
Patent number
US07776905B2

Reaction notes

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