Dichloromethane → 3-Azido-3'-tert-butoxycarbonylbiphenyl

HRID 849303노트

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HRID 849303 반응식
C[C:2]1[CH:3]=[C:4]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH:9]=2)[CH:5]=[CH:6][CH:7]=1.BrN1C(=O)CCC1=O.[N-:29]=[N+:30]=[N-:31].[Na+].C(Cl)Cl>C(Cl)(Cl)(Cl)Cl.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1.O>[N:29]([C:2]1[CH:3]=[C:4]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH:9]=2)[CH:5]=[CH:6][CH:7]=1)=[N+:30]=[N-:31]

참가 물질

8

반응물 4

HCID 6344DichloromethaneHCID 33557Sodium AzideHCID 67184N-bromobutanimideHCID 108018643-Methyl-3'-tert-butoxycarbonylbiphenyl

생성물 1

HCID 195916263-Azido-3'-tert-butoxycarbonylbiphenyl수율 89.1%

시약·촉매·용매 3

HCID 7187Benzoyl Peroxide촉매HCID 962Water용매HCID 5943Carbon Tetrachloride용매

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온도
80 °C

실험 절차

Compound 19 (2.18 g, 8.13 mmol) and N-bromosuccinimide (1.70 g, 9.50 mmol) was suspended in 60 mL of CCl4. Dibenzoyl peroxide (20 mg) was added and the mixture was refluxed for 1.5 hr. After removing the solid, the filtrate was washed with concentrated sodium bicarbonate and dried over sodium sulfate. 1H NMR showed the crude material contained 70% of monobrominated and 30% of dibrominated product. This material was dissolved in 20 mL of DMSO and sodium azide (3.70 g, 57 mmol) was added. The mixture was heated to 80° C. for 4 hr before being poured into a mixture of methylene chloride and water. The organic layer was dried and evaporated. The residue was purified by flash column chromatography (5% of ethyl acetate in hexane) to give 20 (2.14 g, 78%, two steps) as colorless oil. 1H NMR (CDCl3) δ 8.22 (s, 1H), 8.00 (d, 7.7 Hz, 1H), 7.76 (d, 8.2 Hz, 1H), 7.58 (m, 2H), 7.50 (m, 2H), 7.33 (d, 7.6 Hz, 1H), 4.43 (s, 2H), 1.62 (s, 9H). 13C NMR (CDCl3) δ 165.2, 140.5, 140.3, 135.8, 132.3, 130.7, 129.1, 128.5, 128.2, 127.8, 127.1, 126.7, 126.6, 80.9, 54.3, 27.8.

후처리

  1. temperaturethe mixture was refluxed for 1.5 hr
  2. customAfter removing the solid
  3. washthe filtrate was washed with concentrated sodium bicarbonate
  4. dry with materialdried over sodium sulfate
  5. dissolutionThis material was dissolved in 20 mL of DMSO
  6. customThe organic layer was dried
  7. customevaporated
  8. customThe residue was purified by flash column chromatography (5% of ethyl acetate in hexane)

출처 및 근거

ORD 기록
ord-6e07863a183f493e82ed4fe83a44ecb6
출처 데이터셋
uspto-grants-2000_01
특허 번호
US06011175

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