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

HRID 482340

反応式

HRID 482340 の反応式
[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]

参加物

4

反応物 2

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

生成物 1

HCID 11961369Tert-butyl 3-nitrobenzoate収率 63.5%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-be1c5ba31c0b42b58399cd0d291adb63
出典データセット
uspto-grants-1998_08
特許番号
US05795887

関連ノート

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