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

HRID 860559ノート

反応式

HRID 860559 の反応式
[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]

参加物

5

反応物 2

HCID 270626tert-ButylanisoleHCID 21124087Pyridiniumtribromide

生成物 1

HCID 37338984-Bromo-2-tert-butyl-1-methoxybenzene収率 95.5%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6344Dichloromethane溶媒2 回

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-dd7fba94511e47fdb06504b960e675e8
出典データセット
uspto-grants-2006_12
特許番号
US07153875B2

反応ノート

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