Boron tribromide → 2-Amino-4-(4-hydroxyphenyl)thiophene-3-carbonitrile

HRID 1518321노트

반응식

HRID 1518321 반응식
[NH2:1][C:2]1[S:3][CH:4]=[C:5]([C:9]2[CH:14]=[CH:13][C:12]([O:15]CC3C=CC=CC=3)=[CH:11][CH:10]=2)[C:6]=1[C:7]#[N:8].B(Br)(Br)Br>C(Cl)Cl>[NH2:1][C:2]1[S:3][CH:4]=[C:5]([C:9]2[CH:14]=[CH:13][C:12]([OH:15])=[CH:11][CH:10]=2)[C:6]=1[C:7]#[N:8]

참가 물질

4

반응물 2

HCID 25134Boron tribromideHCID 594474742-Amino-4-(4-(benzyloxy)phenyl)thiophene-3-carbonitrile

생성물 1

HCID 152199602-Amino-4-(4-hydroxyphenyl)thiophene-3-carbonitrile수율 83.7%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

To compound 47B (1.1 g, 3.59 mmol) in DCM (80 mL) was added 1.0 M BBr3 (36 mL, 36 mmol) in DCM at rt. A precipitate formed upon addition and gradually disappeared after stirring at rt for 2 hours. The solvent was removed, and the residue was partitioned between water and EtOAc. The organic layer was isolated. The aqueous layer was extracted with EtOAc. The combined organic layers were washed with brine, dried over MgSO4, filtered, and concentrated under reduced pressure. The crude material was purified by column chromatography on silica gel eluting with 3:2/hexanes:EtOAc to provide 0.65 g of the desired product 47C: 1H NMR (DMSO-d6): δ 9.58 (s, 1H), 7.35 (d, J=8.73 Hz, 2H), 7.15 (s, 2H), 6.80 (d, J=8.73 Hz, 2H), 6.34 (s, 1H); MS (ESI(+)): m/z 217 (M+H).

후처리

  1. customA precipitate formed upon addition
  2. customThe solvent was removed
  3. customthe residue was partitioned between water and EtOAc
  4. customThe organic layer was isolated
  5. extractionThe aqueous layer was extracted with EtOAc
  6. washThe combined organic layers were washed with brine
  7. dry with materialdried over MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure
  10. customThe crude material was purified by column chromatography on silica gel eluting with 3:2/hexanes

출처 및 근거

ORD 기록
ord-7ea1b03ea0ca47a9b7f28dbc7cbf787b
출처 데이터셋
uspto-grants-2012_07
특허 번호
US08232273B2

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