tert-Butylanisole → LABOTEST-BB LT00239243

HRID 860559Notes

Reaction equation

HRID 860559 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[O:11][CH3:12])([CH3:4])([CH3:3])[CH3:2].[Br-:13].[Br-].[Br-].[NH+]1C=CC=CC=1.[NH+]1C=CC=CC=1.[NH+]1C=CC=CC=1>C(Cl)Cl.O>[C:1]([C:5]1[CH:10]=[C:9]([Br:13])[CH:8]=[CH:7][C:6]=1[O:11][CH3:12])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 270626tert-ButylanisoleHCID 21124087Pyridiniumtribromide

Product 1

HCID 3733898LABOTEST-BB LT00239243Yield 95.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 2-(t-butyl)anisole (16.38 g, 0.0997 mol) in CH2Cl2 (350 mL) was added pyridinium tribromide (35.09 g, 0.110 mol). The resulting mixture was allowed to stir at RT overnight. The mixture was diluted with CH2Cl2 and H2O and the layers were separated, the aqueous layer was extracted with CH2Cl2 (2×). The combined organic layers were washed with H2O, brine and dried with MgSO4. The mixture was filtered and the solvents evaporated to give 2-(t-butyl)-4-bromoanisole as an oil (23.16 g, 95%). 1H NMR (300 MHz, CDCl3): δ 1.35 (s, 9H), 3.82 (s, 3H), 6.74 (d, J=8.7 Hz, 1H), 7.28 (dd, J1=8.7 Hz, J2=2.4 Hz, 1H), 7.35 (d, J=2.4 Hz, 1H).

Workup

  1. customthe layers were separated
  2. extractionthe aqueous layer was extracted with CH2Cl2 (2×)
  3. washThe combined organic layers were washed with H2O, brine
  4. dry with materialdried with MgSO4
  5. filtrationThe mixture was filtered
  6. customthe solvents evaporated

Sources & evidence

ORD record
ord-dd7fba94511e47fdb06504b960e675e8
Source dataset
uspto-grants-2006_12
Patent number
US07153875B2

Reaction notes

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