Triethylamine → N-(4-bromo-3-nitrophenyl)pivalamide

HRID 1915466Notes

Reaction equation

HRID 1915466 reaction equation
[CH3:1][C:2]([CH3:7])([CH3:6])[C:3](Cl)=[O:4].[Br:8][C:9]1[CH:15]=[CH:14][C:12]([NH2:13])=[CH:11][C:10]=1[N+:16]([O-:18])=[O:17].CCN(CC)CC>C(Cl)Cl>[Br:8][C:9]1[CH:15]=[CH:14][C:12]([NH:13][C:3](=[O:4])[C:2]([CH3:7])([CH3:6])[CH3:1])=[CH:11][C:10]=1[N+:16]([O-:18])=[O:17]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 62493Pivaloyl chlorideHCID 6122994-Bromo-3-nitroaniline

Product 1

HCID 68464766N-(4-bromo-3-nitrophenyl)pivalamideYield 94.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2,2-dimethylpropanoyl chloride (28 g, 232.2 mmol) was added to a stirred solution of 4-bromo-3-nitro-aniline (42 g, 193.5 mmol) and Et3N (51 mL, 366 mmol) in anhydrous DCM (200 mL) at 0° C. under an atmosphere of N2. The cooling bath was removed and the stirring was continued at room temperature for 2 h. The reaction mixture was poured into ice (500 g) and extracted with CH2Cl2. The combined organic layer was dried over Na2SO4 and evaporated in vacuo to afford crude product N-(4-bromo-3-nitrophenyl)pivalamide (55 g, 94%) which was used directly in the next step. 1H NMR (300 MHz, CDCl3) δ: 8.18-8.17 (m, 1H), 7.64-7.63 (m, 2H), 7.50 (br s, 1H), 1.32 (s, 9H).

Workup

  1. customThe cooling bath was removed
  2. additionThe reaction mixture was poured into ice (500 g)
  3. extractionextracted with CH2Cl2
  4. dry with materialThe combined organic layer was dried over Na2SO4
  5. customevaporated in vacuo

Sources & evidence

ORD record
ord-285b600f35b7439d903110e7a175b830
Source dataset
uspto-grants-2013_12
Patent number
US08614327B2

Reaction notes

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