Nitric Acid → 3-Bromo-2-nitro-benzo(b)thiophene

HRID 131370

반응식

HRID 131370 반응식
[N+:1]([O-:4])(O)=[O:2].[Br:5][C:6]1[C:7]2[CH:14]=[CH:13][CH:12]=[CH:11][C:8]=2[S:9][CH:10]=1.C(OCC)(=O)C>C(O)(C(F)(F)F)=O.ClCCl>[Br:5][C:6]1[C:7]2[CH:14]=[CH:13][CH:12]=[CH:11][C:8]=2[S:9][C:10]=1[N+:1]([O-:4])=[O:2]

참가 물질

6

반응물 3

HCID 944Nitric AcidHCID 8857Ethyl AcetateHCID 123250Benzo(b)thiophene, 3-bromo-

생성물 1

HCID 2970503-Bromo-2-nitro-benzo(b)thiophene

시약·촉매·용매 2

HCID 6344Dichloromethane용매2회HCID 6422Trifluoroacetic acid용매

반응 조건

온도
0 °C

실험 절차

Add dropwise fuming nitric acid (90%, 8.6 mL, 183 mmol) to a mixture of 3-bromo benzo[b]thiophene (39 g, 183 mmol) in TFA (100 mL) and dichloromethane (400 mL) at 0° C. The reaction turn greenish, then yellow precipitates. To this reaction mixture, add dichloromethane (200 mL) and the reaction stir at 0° C. for 30 min. Then pour the reaction into ice-water (2L). Extract with dichloromethane (3×500 mL) and the organic layer dry over MgSO4. Evaporation give a yellow solid. The resulting yellow solid triturate with diethyl ether to give a yellow solid. (Total: 34.8 g, 73%). Mass spectrum (m/e): 259(M+1); 1HNMR(300 MHz, DMSO-d6) δ ppm: 7.70(tt, 2H), 8.04(d, 1H), 8.17(d, 1H). 13CNMR(75 MHz, DMSO-d6) δ ppm: 112.5, 124.8, 126.9, 127.9, 131.3, 137.0, 137.2, 166.1.

후처리

  1. additionThen pour
  2. extractionExtract with dichloromethane (3×500 mL)
  3. dry with materialthe organic layer dry over MgSO4
  4. customEvaporation
  5. customgive a yellow solid
  6. customThe resulting yellow solid triturate with diethyl ether
  7. customto give a yellow solid

출처 및 근거

ORD 기록
ord-80b4adacaad34e8898a241a418330c09
출처 데이터셋
uspto-grants-2008_06
특허 번호
US07384934B2

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