2-Iso-propyl-3-methylanisole → HCID 66642817, compound

HRID 1170956Notes

Reaction equation

HRID 1170956 reaction equation
[CH:1]([C:4]1[C:9]([CH3:10])=[CH:8][CH:7]=[CH:6][C:5]=1[O:11][CH3:12])([CH3:3])[CH3:2].[Br-:13].[Br-].[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C([N+](CCCC)(CCCC)CCCC)CCC.C([N+](CCCC)(CCCC)CCCC)CCC>C(Cl)Cl>[Br:13][C:8]1[CH:7]=[CH:6][C:5]([O:11][CH3:12])=[C:4]([CH:1]([CH3:3])[CH3:2])[C:9]=1[CH3:10]

Participants

4

Reactant 2

HCID 210341322-Iso-propyl-3-methylanisoleHCID 23500184Tetra-n-butylammonium tribromide

Product 1

HCID 66642817HCID 66642817, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 2-iso-propyl-3-methylanisole (0.44 g, 2.7 mmol) in CH2Cl2 at room temperature was added a solution of tetrabutylammonium tribromide (1.42 g, 2.94 mmol) in CH2Cl2. The reaction mixture was stirred for 2 h and the solvent was removed under reduced pressure. The crude product was purified by column chromatography on silica gel, eluting with 5% ethyl acetate in hexanes to afford 4-bromo-2-iso-propyl-3-methylanisole as yellowish oil (0.60 g, 92%): 1H NMR (300 MHz, DMSO-d6): δ 7.37 (d, J=13.2 Hz, 1 H), 6.78 (d, J=13.2 Hz, 1 H), 3.74 (s, 3 H), 3.38 (m, 1 H), 2.38 (s, 3 H), 1.25 (d, J=10.8 Hz, 6 H); TLC conditions: Uniplate silica gel, 250 microns; Mobile phase=ethyl acetate-hexanes (5:95); Rf=0.80.

Workup

  1. customthe solvent was removed under reduced pressure
  2. customThe crude product was purified by column chromatography on silica gel
  3. washeluting with 5% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-d68325bb78044f97bc0fe47e9bc6b5aa
Source dataset
uspto-grants-2010_11
Patent number
US07829552B2

Reaction notes

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