Benzoyl chloride, 3-nitro- → Tert-butyl 3-nitrobenzoate

HRID 482340

반응식

HRID 482340 반응식
[CH3:1][C:2]([CH3:5])([O-:4])[CH3:3].[K+].[N+:7]([C:10]1[CH:11]=[C:12]([CH:16]=[CH:17][CH:18]=1)[C:13](Cl)=[O:14])([O-:9])=[O:8]>C1COCC1>[C:2]([O:4][C:13](=[O:14])[C:12]1[CH:16]=[CH:17][CH:18]=[C:10]([N+:7]([O-:9])=[O:8])[CH:11]=1)([CH3:5])([CH3:3])[CH3:1]

참가 물질

4

반응물 2

HCID 8495Benzoyl chloride, 3-nitro-HCID 23665647Potassium tert-butoxide

생성물 1

HCID 11961369Tert-butyl 3-nitrobenzoate수율 63.5%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

Potassium t-butoxide (3.82 g, 32.30 mmol) is added to a solution of 3-nitrobenzoyl chloride (5.00 g, 26.94 mmol) in anhydrous THF (70 mL) and stirred under nitrogen for 2 hrs. The reaction mixture is concentrated in vacuo and partitioned between DCM and water. After separating the phases, the aqueous layer is back-extracted with ethyl acetate. The organic layers are combined, dried over anhydrous magnesium sulfate, filtered and then concentrated in vacuo. The crude product is purified on flash grade silica gel using 0-5% gradient of ethyl acetate in n-hexane. Fractions containing the product are combined, concentrated in vacuo, and then dried under high vacuum to provide the title compound as an oil (3.82 g, 17.1 mmol). 1H NMR (300 MHz, CDCl3) δ=1.63 (s, 9H); 7.62 (t, J=7.9 Hz, 1H); 8.29-8.41 (m, 2H); 8.78-8.80 (m, 1H). MS (Cl): [M+H]+ =224.

후처리

  1. concentrationThe reaction mixture is concentrated in vacuo
  2. custompartitioned between DCM and water
  3. customAfter separating the phases
  4. extractionthe aqueous layer is back-extracted with ethyl acetate
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe crude product is purified on flash grade silica gel using 0-5% gradient of ethyl acetate in n-hexane
  9. additionFractions containing the product
  10. concentrationconcentrated in vacuo
  11. customdried under high vacuum

출처 및 근거

ORD 기록
ord-be1c5ba31c0b42b58399cd0d291adb63
출처 데이터셋
uspto-grants-1998_08
특허 번호
US05795887

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