Boron tribromide → 2-(2-Hydroxy-4-nitrophenyl)benzothiazole

HRID 339497ノート

反応式

HRID 339497 の反応式
C[O:2][C:3]1[CH:8]=[C:7]([N+:9]([O-:11])=[O:10])[CH:6]=[CH:5][C:4]=1[C:12]1[S:13][C:14]2[CH:20]=[CH:19][CH:18]=[CH:17][C:15]=2[N:16]=1.B(Br)(Br)Br>C(Cl)Cl>[OH:2][C:3]1[CH:8]=[C:7]([N+:9]([O-:11])=[O:10])[CH:6]=[CH:5][C:4]=1[C:12]1[S:13][C:14]2[CH:20]=[CH:19][CH:18]=[CH:17][C:15]=2[N:16]=1

参加物

4

反応物 2

HCID 25134Boron tribromideHCID 672372802-(2-Methoxy-4-nitrophenyl)benzothiazole

生成物 1

HCID 1360605262-(2-Hydroxy-4-nitrophenyl)benzothiazole収率 99%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

Prepared as described in the Demethylation section above using 2-(2-methoxy-4-nitrophenyl)benzothiazole (0.5 g, 1.75 mmol) in dry DCM (30 ml) was added dropwise at room temperature and BBr3 (1.0 M solution in DCM, 8.8 ml, 8.8 mmol). The reaction mixture was stirred at room temperature for 18 h. The reaction was quenched by addition of MeOH (5 ml) and extracted with 8% w/v NaOH (5×35 ml). The combined aqueous extracts were acidified with 6 M HCl and extracted with EtOAc (3×70 ml). The combined organic extracts were washed with brine (40 ml), dried (Na2SO4) and the solvent removed under reduced pressure to give a solid which was purified by flash chromatography (1:1 Hexane/EtOAc) to give the title compound (0.47 g, 99%) as a pale yellow solid after work-up and flash chromatography (1:1 Hexane/EtOAc).

後処理

  1. customPrepared
  2. additionwas added dropwise at room temperature
  3. customThe reaction was quenched by addition of MeOH (5 ml)
  4. extractionextracted with 8% w/v NaOH (5×35 ml)
  5. extractionextracted with EtOAc (3×70 ml)
  6. washThe combined organic extracts were washed with brine (40 ml)
  7. dry with materialdried (Na2SO4)
  8. customthe solvent removed under reduced pressure
  9. customto give a solid which
  10. customwas purified by flash chromatography (1:1 Hexane/EtOAc)

出典と根拠

ORDレコード
ord-6703bc673ec8421abc37a13bb0317d19
出典データセット
uspto-grants-2014_11
特許番号
US08895313B2

反応ノート

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