Tert-Butylamine → 2-bromo-N-tert-butyl-3-nitrobenzamide

HRID 2036611Notes

Reaction equation

HRID 2036611 reaction equation
[Br:1][C:2]1[C:10]([N+:11]([O-:13])=[O:12])=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=O.[C:14]([NH2:18])([CH3:17])([CH3:16])[CH3:15].CCN(C(C)C)C(C)C.C1CN([P+](ON2N=NC3C2=CC=CC=3)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F>CN(C=O)C.CCOC(C)=O>[Br:1][C:2]1[C:10]([N+:11]([O-:13])=[O:12])=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([NH:18][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:6]

Participants

7

Reactant 4

HCID 6385Tert-ButylamineHCID 684522-Bromo-3-nitrobenzoic acidHCID 81531DiisopropylethylamineHCID 2724699PyBOP

Product 1

HCID 674309942-bromo-N-tert-butyl-3-nitrobenzamide

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 2-bromo-3-nitrobenzoic acid (500 mg, 2.03 mmol) in DMF (3 mL) was added tert-butylamine (0.22 mL, 2.04 mmol), 1,1′-dimethyltriethylamine (0.71 mL, 4.1 mmol) and (1H-benzo[d][1,2,3]triazol-1-yloxy)tripyrrolidin-1-ylphosphonium hexafluorophosphate(V) (1.27 g, 2.44 mmol). The resulting mixture was stirred at rt for 2 h. The reaction mixture was diluted with EtOAc, washed with water, brine, dried over magnesium sulfate and concentrated in vacuo. The residue was purified by flash chromatography on silica gel using 0 to 100% gradient of EtOAC:DCM (1:1) in DCM as eluent to give 2-bromo-N-tert-butyl-3-nitrobenzamide: 1H NMR (400 MHz, CDCl3) δ 7.74 (1H, dd, J=8.0, 4.0 Hz), 7.62 (1H, d, J=8.0 Hz), 7.51 (1H, t, J=8.0 Hz), 5.62 (1H, br), 1.52 (9H, s); LC-MS (ESI) m/z 301.0 [M+H]+.

Workup

  1. washwashed with water, brine
  2. dry with materialdried over magnesium sulfate
  3. concentrationconcentrated in vacuo
  4. customThe residue was purified by flash chromatography on silica gel using 0 to 100% gradient of EtOAC

Sources & evidence

ORD record
ord-765b68203cd34cafbb24cfe4ef0dcc3b
Source dataset
uspto-grants-2013_11
Patent number
US08575183B2

Reaction notes

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