4-tert-Butylbenzoyl chloride → 4-tert-butyl-N-(2,3-dibromophenyl)benzamide

HRID 491427Notes

Reaction equation

HRID 491427 reaction equation
[Br:1][C:2]1[C:8]([Br:9])=[CH:7][CH:6]=[CH:5][C:3]=1[NH2:4].[C:10]([C:14]1[CH:22]=[CH:21][C:17]([C:18](Cl)=[O:19])=[CH:16][CH:15]=1)([CH3:13])([CH3:12])[CH3:11].C(N(C(C)C)CC)(C)C>O1CCOCC1>[C:10]([C:14]1[CH:15]=[CH:16][C:17]([C:18]([NH:4][C:3]2[CH:5]=[CH:6][CH:7]=[C:8]([Br:9])[C:2]=2[Br:1])=[O:19])=[CH:21][CH:22]=1)([CH3:13])([CH3:11])[CH3:12]

Participants

5

Reactant 3

HCID 743724-tert-Butylbenzoyl chlorideHCID 81531DiisopropylethylamineHCID 155799982,3-Dibromobenzenamine

Product 1

HCID 576782944-tert-butyl-N-(2,3-dibromophenyl)benzamide

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

The amide was prepared according to Example 18 from 2,3-dibromoaniline, 4-tert-butylbenzoyl chloride and diisopropylethylamine in dioxane. MS (ESI) m/z 408; HPLC Method B, purity 80.6% at 210-370 nm, 11.4 min.; 74.9% at 240 nm, 11.4 min.; HRMS: calcd for C17H17Br2NO+H+, 409.97496; found (ESI, [M+H]+), 409.9775.

Workup

  1. customat 210-370 nm, 11.4 min.
  2. customat 240 nm, 11.4 min.

Sources & evidence

ORD record
ord-abd9a5dbcd4f462f933b1e234c1bc8b2
Source dataset
uspto-grants-2009_05
Patent number
US07531542B2

Reaction notes

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