Sodium Hydroxide → HCID 10706982, compound

HRID 883079Notes

Reaction equation

HRID 883079 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([NH2:8])=[CH:4][C:3]=1[CH3:9].[OH-].[Na+].[CH3:12][C:13]([CH3:18])=[CH:14][C:15](Cl)=[O:16]>C(Cl)Cl>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:15](=[O:16])[CH:14]=[C:13]([CH3:18])[CH3:12])=[CH:4][C:3]=1[CH3:9]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 233594-Bromo-3-methylanilineHCID 1023943-Methyl-2-butenoyl chloride

Product 1

HCID 10706982HCID 10706982, compoundYield 98.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

In accordance with Scheme 15, to the solution of 4-bromo-3-methyl-phenylamine (2 g, 1 eq.) in 5 mL of CH2Cl2 was added 10 mL of 2 M NaOH followed by dropwise addition of 3,3-dimethylacryloyl chloride (1.32 mL, 1.1 eq.) in 5 mL of CH2Cl2. The reaction was allowed to stir overnight and then partitioned between EtOAc and brine. The organic layer was separated, dried over Na2SO4, filtered and the solvent was removed in vacuo to afford 2.84 g (98.6%) of product Compound 53A as beige solid. Crude product was used for the next step.

Workup

  1. custompartitioned between EtOAc and brine
  2. customThe organic layer was separated
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-d1a7ceaa8a454e0ab19d7af2ce9dda0a
Source dataset
uspto-grants-2012_08
Patent number
US08236819B2

Reaction notes

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