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

HRID 482340

Reaction equation

HRID 482340 reaction equation
[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]

Participants

4

Reactant 2

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

Product 1

HCID 11961369Tert-butyl 3-nitrobenzoateYield 63.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-be1c5ba31c0b42b58399cd0d291adb63
Source dataset
uspto-grants-1998_08
Patent number
US05795887

Linked notes

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