Benzoyl chloride, 2-chloro-4-nitro- → tert-Butyl 2-chloro-4-nitrobenzoate

HRID 1660867Notes

Reaction equation

HRID 1660867 reaction equation
[Li+].[CH3:2][C:3]([O-:6])([CH3:5])[CH3:4].[Cl:7][C:8]1[CH:16]=[C:15]([N+:17]([O-:19])=[O:18])[CH:14]=[CH:13][C:9]=1[C:10](Cl)=[O:11]>O1CCCC1>[Cl:7][C:8]1[CH:16]=[C:15]([N+:17]([O-:19])=[O:18])[CH:14]=[CH:13][C:9]=1[C:10]([O:6][C:3]([CH3:5])([CH3:4])[CH3:2])=[O:11]

Participants

4

Reactant 2

HCID 81522Benzoyl chloride, 2-chloro-4-nitro-HCID 236647642-Propanol, 2-methyl-, lithium salt (1:1)

Product 1

HCID 22593093tert-Butyl 2-chloro-4-nitrobenzoateYield 88%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Lithium tert-butylate (2.2 M in tetrahydrofuran, 6.2 mL, 13.6 mmol) was added to a solution of 2-chloro-4-nitrobenzoyl chloride (2.00 g, 9.09 mmol) in tetrahydrofuran (12 mL) at 0° C. The orange solution was kept at 0° C. for 1.5 h, then allowed to reach room temperature over 16 h, then partitioned between 1 M aq. sodium carbonate solution and isopropyl acetate. The organic layer was dried (MgSO4) and evaporated to afford tert-butyl 2-chloro-4-nitro-benzoate (2.05 g, 88%) which was directly used in the next step. Brown oil, MS (EI)=257.1 (M+).

Workup

  1. waitto reach room temperature over 16 h
  2. custompartitioned between 1 M aq. sodium carbonate solution and isopropyl acetate
  3. dry with materialThe organic layer was dried (MgSO4)
  4. customevaporated

Sources & evidence

ORD record
ord-9ee1bf84c55f45a2acb73dbc586062c9
Source dataset
uspto-grants-2011_10
Patent number
US08030308B2

Reaction notes

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