Benzene → Ijrzsljquollsz-uhfffaoysa-

HRID 589004

반응식

HRID 589004 반응식
[Al](Br)(Br)Br.[CH:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.[OH:11][C:12]1[CH:13]=[CH:14][CH:15]=[C:16]2[C:21]=1[N:20]=[CH:19][CH:18]=[CH:17]2.Br.Cl>>[C:5]1([CH:14]2[CH2:13][C:12](=[O:11])[C:21]3[N:20]=[CH:19][CH:18]=[CH:17][C:16]=3[CH2:15]2)[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1

참가 물질

6

반응물 5

HCID 241BenzeneHCID 260Hydrogen BromideHCID 313Hydrochloric AcidHCID 19238-HydroxyquinolineHCID 24409Aluminum bromide

생성물 1

HCID 12036201Ijrzsljquollsz-uhfffaoysa-

반응 조건

온도
40 °C

실험 절차

To a stirred suspension of AlBr3 (4.80 g, 18 mmol) in benzene (4.8 mL, 55 mmol) was added 8-hydroxyquinoline (0.50 g, 3.4 mmol). The resulting mixture was saturated with HBr (g) and then stirred at 40° C. for 48 h. The reaction mixture was cooled to ambient temperature and poured onto ice (50 g). The resulting mixture was adjusted to pH=1-2 by addition of concentrated HCl and then was extracted with EtOAc (3×20 mL), discarding the organic extracts. The aqueous layer was adjusted to pH 12 by addition of NaOH (s), keeping the temperature below 10° C., and was then extracted with EtOAc (3×20 mL). These combined organic extracts were washed with brine (30 mL), dried over sodium sulfate, filtered, and concentrated in vacuo to give the title compound in sufficient purity for use in the next step. MS: m/z=223.8 (M+1).

후처리

  1. temperatureThe reaction mixture was cooled to ambient temperature
  2. additionpoured onto ice (50 g)
  3. extractionwas extracted with EtOAc (3×20 mL)
  4. additionThe aqueous layer was adjusted to pH 12 by addition of NaOH (s)
  5. customthe temperature below 10° C.
  6. extractionwas then extracted with EtOAc (3×20 mL)
  7. washThese combined organic extracts were washed with brine (30 mL)
  8. dry with materialdried over sodium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-c51cf7a87f24409c9eca2cbe59d0345b
출처 데이터셋
uspto-grants-2016_01
특허 번호
US09227973B2

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