4-tert-Butyltoluene → 4-Tert-butyl-2-chloro-1-methylbenzene

HRID 1927394Notes

Reaction equation

HRID 1927394 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([CH3:11])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].I([Cl:15])(=O)=O.I(Cl)(=O)=O.I(Cl)(=O)=O.I(Cl)(=O)=O.C([N+](C)(C)C)C1C=CC=CC=1>>[C:1]([C:5]1[CH:6]=[CH:7][C:8]([CH3:11])=[C:9]([Cl:15])[CH:10]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

3

Reactant 2

HCID 73904-tert-ButyltolueneHCID 57347110Benyltrimethylammonium tetrachloroiodate

Product 1

HCID 5243374-Tert-butyl-2-chloro-1-methylbenzeneYield 62.3%

Conditions

Temperature
70 °C

Procedure

A solution of 2 g (13.49 mmol) of 4-tert-butyltoluene is mixed with 5.65 g (13.49 mmol) of benzyltrimethylammonium tetrachloroiodate and stirred at 70° C. for 24 hours. After cooling, the precipitate is filtered off with suction and the filtrate is concentrated. The resulting residue is purified over silica gel (mobile phase: cyclohexane). 1.53 g (8.4 mmol) of the title compound are obtained.

Workup

  1. temperatureAfter cooling
  2. filtrationthe precipitate is filtered off with suction
  3. concentrationthe filtrate is concentrated
  4. customThe resulting residue is purified over silica gel (mobile phase: cyclohexane)

Sources & evidence

ORD record
ord-6aa77afc762a42ec8d6e4b1ed64ec8ef
Source dataset
uspto-grants-2012_05
Patent number
US08183271B2

Reaction notes

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