tert-Butylanisole → 4-Bromo-2-tert-butyl-1-methoxybenzene

HRID 860559노트

반응식

HRID 860559 반응식
[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]

참가 물질

5

반응물 2

HCID 270626tert-ButylanisoleHCID 21124087Pyridiniumtribromide

생성물 1

HCID 37338984-Bromo-2-tert-butyl-1-methoxybenzene수율 95.5%

시약·촉매·용매 2

HCID 962Water용매HCID 6344Dichloromethane용매2회

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-dd7fba94511e47fdb06504b960e675e8
출처 데이터셋
uspto-grants-2006_12
특허 번호
US07153875B2

반응 노트

불러오는 중…