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2,6-Dichlorotoluene → 2,6-Dichlorobenzyltriphenylphosphonium bromide

HRID 11066
Notes
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Reaction equation

HRID 11066 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[CH3:9].[Br:10]N1C(=O)CCC1=O.[C:18]1([P:24]([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>C1C=CC=CC=1.N(C(C)(C)C#N)=NC(C)(C)C#N>[Br-:10].[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[CH2:9][P+:24]([C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1)([C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)[C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 83682,6-DichlorotolueneHCID 11776TriphenylphosphineHCID 67184N-bromobutanimide

Product 1

HCID 118435512,6-Dichlorobenzyltriphenylphosphonium bromideYield 99%

Reagents, catalysts & solvents 2

HCID 6547AzobisisobutyronitrileCatalyst
HCID 241
Benzene
Solvent

Procedure

A mixture of 2,6-dichlorotoluene (20.1 g, 0.125 mol), N-bromosuccinimide (24.6 g, 0.138 mol) and 2,2′-azobisisobutyronitrile (0.41 g, 2.50 mmol) in dry benzene (300 mL) under N2 was stirred at reflux for 6 h with continuous irradiation from a 100W lamp. The resulting reaction mixture was concentrated under vacuum (to 50 mL), cooled and filtered, washing with dry benzene. The filtrate (containing the crude benzyl bromide) was treated directly with triphenylphosphine (49.3 g, 0.188 mol), stirring at reflux for 17 h. After cooling, the precipitate was collected by filtration, washing thoroughly with dry benzene, then pentane, and dried under vacuum at 50° C. to give the phosphonium salt (511) as a cream powder (62.1 g, 99%), mp (benzene) 247–250° C. 1H NMR (CDCl3) δ 7.76 (m, 9H), 7.64 (m, 6H), 7.18 (s, 3H), 5.50 (d, J=14.3 Hz, 2H). Found: C, 60.03; H, 3.76. C25H2,BRCl2P requires C, 59.79; H, 4.01.

Workup

  1. customThe resulting reaction mixture
  2. concentrationwas concentrated under vacuum (to 50 mL)
  3. temperaturecooled
  4. filtrationfiltered
  5. washwashing with dry benzene
  6. additionThe filtrate (containing the crude benzyl bromide)
  7. stirringstirring
  8. temperatureat reflux for 17 h
  9. temperatureAfter cooling
  10. filtrationthe precipitate was collected by filtration
  11. washwashing thoroughly with dry benzene
  12. dry with materialpentane, and dried under vacuum at 50° C.

Sources & evidence

ORD record
ord-60c9c68580eb4ab0aadc7efe56b5175a
Source dataset
uspto-grants-2006_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07094798B1

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes