Hydrochloric Acid → HCID 59637336, 화합물

HRID 1842861노트

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HRID 1842861 반응식
Cl[CH:2]([CH:8]1[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]1)[C:3]([O:5][CH2:6][CH3:7])=[O:4].[F:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[N+:21]([O-:23])=[O:22].Cl>CN(C=O)C.O>[CH:8]1([CH:2]([C:19]2[CH:18]=[CH:17][C:16]([N+:21]([O-:23])=[O:22])=[C:15]([F:14])[CH:20]=2)[C:3]([O:5][CH2:6][CH3:7])=[O:4])[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]1

참가 물질

6

반응물 3

HCID 313Hydrochloric AcidHCID 738951-Fluoro-2-nitrobenzeneHCID 13215910HCID 13215910, 화합물

생성물 1

HCID 59637336HCID 59637336, 화합물수율 49%

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

반응 조건

온도
-45 °C

실험 절차

8.2 g of potassium tert.butylate were dissolved in 70 ml of DMF and cooled to −45° C. For this purpose, a mix of ethyl 2-chloro-2-cyclohexylacetate (36.6 mmol, 7.5 g) and 1-fluoro-2-nitrobenzene (36.6 mmol, 3.9 ml) was carefully added dropwise and stirred for a further 20 minutes. The reaction mix was set to pH 4 using 16% HCl, diluted with 25 ml of water and extracted with EtOAc (3×50 ml). Once combined, the organic phases were washed with water and sat. aq. NaCl sol., dried over MgSO4 and concentrated under vacuum. The resulting residue was purified by column chromatography (silica gel: mesh 100-200, eluent: 10% EtOAc in cyclohexane) and produced 5.5 g (49%) of product.

후처리

  1. additionwas carefully added dropwise
  2. additionThe reaction mix
  3. extractionextracted with EtOAc (3×50 ml)
  4. washthe organic phases were washed with water and sat. aq. NaCl sol.
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated under vacuum
  7. customThe resulting residue was purified by column chromatography (silica gel: mesh 100-200, eluent: 10% EtOAc in cyclohexane)

출처 및 근거

ORD 기록
ord-38817994863b4e16b0c3ffa8aab63b5d
출처 데이터셋
uspto-grants-2015_02
특허 번호
US08946204B2

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