Water → 4-bromo-3-chloro-N-trimethylsilanylmethyl-benzamide

HRID 241517

Reaction equation

HRID 241517 reaction equation
[Br:1][C:2]1[CH:10]=[CH:9][C:5]([C:6](O)=[O:7])=[CH:4][C:3]=1[Cl:11].[NH2:12][CH2:13][Si:14]([CH3:17])([CH3:16])[CH3:15].O>C(Cl)Cl>[Br:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([NH:12][CH2:13][Si:14]([CH3:17])([CH3:16])[CH3:15])=[O:7])=[CH:4][C:3]=1[Cl:11]

Participants

5

Reactant 3

HCID 962WaterHCID 874881-(Trimethylsilyl)methylamineHCID 125943024-Bromo-3-chlorobenzoic acid

Product 1

HCID 668366994-bromo-3-chloro-N-trimethylsilanylmethyl-benzamideYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
20 °C

Procedure

To a suspension of 4-bromo-3-chlorobenzoic acid (25.00 g, 106.2 mmol) in CH2Cl2 (320 mL) was added N,N-dimethyl aminopyridine (1.95 g), followed by N-ethyl-N-dimethylamine propylcarbodiimide hydrochloride (22.39 g) in small portions. After 30 min at room temperature, aminomethyl trimethylsilane (11.2 g, 7.87 mL, 108 mmol) was added while maintaining the temperature at 20° C. After stirring over night, water was added and the organic layer was separated. The aqueous layer was extracted twice with CH2Cl2 and the combined organic phases were dried and evaporated in vacuum. The residue was purified by flash chromatography on silica gel to give the title compound (34.00 g, 100%).

Workup

  1. customthe organic layer was separated
  2. extractionThe aqueous layer was extracted twice with CH2Cl2
  3. customthe combined organic phases were dried
  4. customevaporated in vacuum
  5. customThe residue was purified by flash chromatography on silica gel

Sources & evidence

ORD record
ord-e86fb4dcd46743ff948c85722bfc7573
Source dataset
uspto-grants-2014_02
Patent number
US08653000B2

Linked notes

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