Boron tribromide → 4-Bromo-5-chloro-2-(2,3,4,5-tetrahydro-benzo[b]azepine-1-sulfonyl)-phenol

HRID 2382686ノート

反応式

HRID 2382686 の反応式
[Br:1][C:2]1[C:3]([Cl:24])=[CH:4][C:5]([O:22]C)=[C:6]([S:8]([N:11]2[CH2:17][CH2:16][CH2:15][CH2:14][C:13]3[CH:18]=[CH:19][CH:20]=[CH:21][C:12]2=3)(=[O:10])=[O:9])[CH:7]=1.B(Br)(Br)Br>C(Cl)Cl>[Br:1][C:2]1[C:3]([Cl:24])=[CH:4][C:5]([OH:22])=[C:6]([S:8]([N:11]2[CH2:17][CH2:16][CH2:15][CH2:14][C:13]3[CH:18]=[CH:19][CH:20]=[CH:21][C:12]2=3)(=[O:10])=[O:9])[CH:7]=1

参加物

4

反応物 2

HCID 25134Boron tribromideHCID 684691311-(5-bromo-4-chloro-2-methoxy-benzenesulfonyl)-2,3,4,5-tetrahydro-1H-benzo[b]azepine

生成物 1

HCID 684721004-Bromo-5-chloro-2-(2,3,4,5-tetrahydro-benzo[b]azepine-1-sulfonyl)-phenol収率 91.2%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

To a solution of DCM (25.0 mL) containing 1-(5-bromo-4-chloro-2-methoxy-benzenesulfonyl)-2,3,4,5-tetrahydro-1H-benzo[b]azepine (2.15 g, 5 mmol) at −78° C. was added BBr3 (12.5 mL, 1M in DCM, 12.5 mmol) dropwise. The mixture was gradually warmed to rt while it was stirred for 4 hrs. The mixture was concentrated and partitioned between ethyl acetate (100 mL) and sat. NaHCO3 solution (100 mL). The organic layer was further washed with brine (2×50 mL), dried over MgSO4, and evaporated. The purification of the crude material by silica gel column chromatography eluting with hexane/ethyl acetate (6/1) yielded 4-bromo-5-chloro-2-(2,3,4,5-tetrahydro-benzo[b]azepine-1-sulfonyl)-phenol as a white solid (1.9 g). NMR (CDCl3), δ, 7.739 (1H, s), 7.186-7.259 (4H, m), 7.127 (1H, s), 3.692 (2H, m), 2.502-2.539 (2H, m), 1.802-1.868 (2H, m), 1.601-1.676 (2H, m).

後処理

  1. concentrationThe mixture was concentrated
  2. custompartitioned between ethyl acetate (100 mL) and sat. NaHCO3 solution (100 mL)
  3. washThe organic layer was further washed with brine (2×50 mL)
  4. dry with materialdried over MgSO4
  5. customevaporated
  6. customThe purification of the crude material by silica gel column chromatography
  7. washeluting with hexane/ethyl acetate (6/1)

出典と根拠

ORDレコード
ord-505cdba1272c43199edfc4831c88a4ad
出典データセット
uspto-grants-2012_09
特許番号
US08263588B2

反応ノート

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