Hydrochloric Acid → HCID 59637336, 화합물

HRID 1027966노트

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HRID 1027966 반응식
CC([O-])(C)C.[K+].Cl[CH:8]([CH:14]1[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]1)[C:9]([O:11][CH2:12][CH3:13])=[O:10].[F:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=1[N+:27]([O-:29])=[O:28].Cl>CN(C=O)C.O>[CH:14]1([CH:8]([C:25]2[CH:24]=[CH:23][C:22]([N+:27]([O-:29])=[O:28])=[C:21]([F:20])[CH:26]=2)[C:9]([O:11][CH2:12][CH3:13])=[O:10])[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]1

참가 물질

7

반응물 4

HCID 313Hydrochloric AcidHCID 738951-Fluoro-2-nitrobenzeneHCID 13215910HCID 13215910, 화합물HCID 23665647Potassium tert-butoxide

생성물 1

HCID 59637336HCID 59637336, 화합물수율 49%

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

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온도
-45 °C

실험 절차

8.2 g of potassium tert-butylate were dissolved in 70 mL of DMF and cooled to −45° C. To this, a mixture of ethyl 2-chloro-2-cyclohexylacetate (36.6 mmol, 7.5 g) and 1-fluoro-2-nitrobenzene (36.6 mmol, 3.9 mL) was gently added dropwise and stirring was continued for a further 20 minutes. The reaction mixture was set to pH 4 with 16% strength aq. HCl, diluted with 25 mL of water, and extracted with EA (3×50 mL). After combining the organic phases, they were washed with water and sat. aq. NaCl solution, dried over MgSO4, and concentrated in vacuo. The resulting residue was purified by column chromatography (silica gel: mesh 100-200, eluent: 10% EA in cyclohexane) and yielded 5.5 g (49%) of the desired product.

후처리

  1. additionwas gently added dropwise
  2. extractionextracted with EA (3×50 mL)
  3. washwere washed with water and sat. aq. NaCl solution
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated in vacuo
  6. customThe resulting residue was purified by column chromatography (silica gel: mesh 100-200, eluent: 10% EA in cyclohexane)

출처 및 근거

ORD 기록
ord-e74e165738674d408b9ffec3e4d7135a
출처 데이터셋
uspto-grants-2014_05
특허 번호
US08735426B2

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