Pivaloyl chloride → Methyl 3-bromo-6-(2,2-dimethylpropionyl-amino)-2-nitrobenzoate

HRID 715989Notes

Reaction equation

HRID 715989 reaction equation
[CH3:1][C:2]([CH3:7])([CH3:6])[C:3](Cl)=[O:4].[NH2:8][C:9]1[C:14]([C:15]([O:17][CH3:18])=[O:16])=[C:13]([N+:19]([O-:21])=[O:20])[C:12]([Br:22])=[CH:11][CH:10]=1>N1C=CC=CC=1.C(Cl)Cl>[Br:22][C:12]1[C:13]([N+:19]([O-:21])=[O:20])=[C:14]([C:9]([NH:8][C:3](=[O:4])[C:2]([CH3:7])([CH3:6])[CH3:1])=[CH:10][CH:11]=1)[C:15]([O:17][CH3:18])=[O:16]

Participants

5

Reactant 2

HCID 62493Pivaloyl chlorideHCID 66685320Methyl 6-amino-3-bromo-2-nitrobenzoate

Product 1

HCID 70982880Methyl 3-bromo-6-(2,2-dimethylpropionyl-amino)-2-nitrobenzoateYield 90.7%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6344DichloromethaneSolvent

Procedure

Trimethylacetyl chloride (5.09 g) was added to a solution of methyl 6-amino-3-bromo-2-nitro-benzoate (prepared according to Brock et al Tertrahedron, 1963, 19, 1911, 7.74 g) in pyridine (40 mL) and DCM (40 mL) and left to stand at room temperature for 3 hours. The mixture was concentrated in vacuo and the residue was dissolved in DCM and 1M hydrochloric acid and filtered through a phase separator. The filtrate was concentrated in vacuo and the residue was triturated with pentane. The solid was filtered to give methyl 3-bromo-6-(2,2-dimethylpropionyl-amino)-2-nitrobenzoate (9.17 g).

Workup

  1. waitleft
  2. concentrationThe mixture was concentrated in vacuo
  3. dissolutionthe residue was dissolved in DCM
  4. filtration1M hydrochloric acid and filtered through a phase separator
  5. concentrationThe filtrate was concentrated in vacuo
  6. customthe residue was triturated with pentane
  7. filtrationThe solid was filtered

Sources & evidence

ORD record
ord-cec44a9c6c8d4291b8f55a7f1e22f61c
Source dataset
uspto-grants-2015_11
Patent number
US09187494B2

Reaction notes

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