Triethylamine → 4-bromo-N,N-dimethylbenzamide

HRID 1643604Notes

Reaction equation

HRID 1643604 reaction equation
[Br:1][C:2]1[CH:10]=[CH:9][C:5]([C:6](Cl)=[O:7])=[CH:4][CH:3]=1.Cl.[CH3:12][NH:13][CH3:14].C(N(CC)CC)C>C(Cl)Cl>[Br:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([N:13]([CH3:14])[CH3:12])=[O:7])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 10473Dimethylamine, hydrochlorideHCID 685154-Bromobenzoyl chloride

Product 1

HCID 1403894-bromo-N,N-dimethylbenzamideYield 83.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-bromobenzoyl chloride (2.00 g, 9.11 mmol) and dimethyl amine hydrochloride (892 mg, 10.90 mmol) in 20 mL of CH2Cl2 was added triethylamine (3.81 mL, 27.30 mmol). The mixture was stirred at room temperature for 2 h, quenched with water, extracted with 3×CHCl3, dried with Na2SO4, concentrated and purified by Biotage column chromatography with 1-4% MeOH in 1:1 EtOAc/CH2Cl2 to give a white solid (1.73 g, 83% yield). 1H NMR (400 MHz, CDCl3) δ 7.48-7.65 (m, 2 H) 7.20-7.37 (m, 2 H) 3.05 (d, J=50.78 Hz, 6 H); LCMS for C9H10BrNO m/z 228.00 and 230.00 (M+H)+

Workup

  1. customquenched with water
  2. extractionextracted with 3×CHCl3
  3. dry with materialdried with Na2SO4
  4. concentrationconcentrated
  5. custompurified by Biotage column chromatography with 1-4% MeOH in 1:1 EtOAc/CH2Cl2

Sources & evidence

ORD record
ord-99803e279ec64375adfa92b7e8d2b007
Source dataset
uspto-grants-2012_02
Patent number
US08119624B2

Reaction notes

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