Acetic Acid → 2-Bromo-N-methyl-N-(1-methylethyl)benzenamine

HRID 215935Notes

Reaction equation

HRID 215935 reaction equation
[Br:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[NH:4][CH3:5].[CH3:10][C:11]([CH3:13])=O.CC(O)=O.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+].[OH-].[Na+]>ClC(Cl)C>[Br:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[N:4]([CH:11]([CH3:13])[CH3:10])[CH3:5]

Participants

7

Reactant 5

HCID 176Acetic AcidHCID 180AcetoneHCID 14798Sodium HydroxideHCID 3340862-Bromo-N-methylanilineHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 534013872-Bromo-N-methyl-N-(1-methylethyl)benzenamine

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Procedure

To a solution of 2-bromo-N-methylaniline (2.07 g, 11.22 mmol), in dichloroethane (45 mL) was added acetone (1.31 g, 22.5 mmol), AcOH (4.04 g, 67.32 mmol) and Na(OAc)3BH (7.14 g, 33.66 mmol) sequentially at RT. The mixture was stirred for 72 h. The reaction was cooled with ice bath, and 2M NaOH (100 mL) was added slowly, then stirred for 5 min. The organic layer was separated, washed with brine dried and solvent removed. The crude product contained a mixture of 2:1 ratio of Compound 219 and starting material. This mixture was used as is in the next step.

Workup

  1. temperatureThe reaction was cooled with ice bath
  2. stirringstirred for 5 min
  3. customThe organic layer was separated
  4. washwashed with brine
  5. customdried
  6. customsolvent removed
  7. additiona mixture of 2:1 ratio of Compound 219

Sources & evidence

ORD record
ord-b40fae3a74b3484a8e37dbb7e1e0cc10
Source dataset
uspto-grants-2012_06
Patent number
US08193203B2

Reaction notes

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