Hydrochloric Acid → N-(2-bromo-4,5-dimethoxyphenyl)pivalamide

HRID 1191327Notes

Reaction equation

HRID 1191327 reaction equation
[Br:1][C:2]1[CH:8]=[C:7]([O:9][CH3:10])[C:6]([O:11][CH3:12])=[CH:5][C:3]=1[NH2:4].[OH-].[Na+].[C:15](Cl)(=[O:20])[C:16]([CH3:19])([CH3:18])[CH3:17].Cl>O.C(OC)(C)(C)C>[Br:1][C:2]1[CH:8]=[C:7]([O:9][CH3:10])[C:6]([O:11][CH3:12])=[CH:5][C:3]=1[NH:4][C:15](=[O:20])[C:16]([CH3:19])([CH3:18])[CH3:17]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 62493Pivaloyl chlorideHCID 4140762-Bromo-4,5-dimethoxyaniline

Product 1

HCID 66849105N-(2-bromo-4,5-dimethoxyphenyl)pivalamide

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 15413tert-Butyl methyl etherSolvent

Procedure

A dry 500 mL three-necked flask was charged with 2-bromo-4,5-dimethoxyaniline (23.4 g, 0.10 mol) and t-BuOMe (200 mL), NaOH (25.3 g, 25%, 0.158 mol) was added in portions at 0° C. Then pivaloyl chloride (12.9 g, 0.106 mol) was added dropwise slowly under N2 at 0° C. After addition, the mixture was stirred for an additional 1 hour and diluted with water (100 mL), acidified by 5% HCl to pH=7 and extracted with EtOAc (100 mL×3). The combined organic layers were washed with water (100 mL×3), dried over anhydrous MgSO4, filtrated and concentrated in vacuum to afford the compound N-(2-bromo-4,5-dimethoxyphenyl)-2,2-dimethylpropanamide. MS (M+H)=316 and 318.

Workup

  1. additionwas added in portions at 0° C
  2. additionAfter addition
  3. extractionextracted with EtOAc (100 mL×3)
  4. washThe combined organic layers were washed with water (100 mL×3)
  5. dry with materialdried over anhydrous MgSO4
  6. filtrationfiltrated
  7. concentrationconcentrated in vacuum

Sources & evidence

ORD record
ord-274eb74ecd424436bcdbd270491d64ae
Source dataset
uspto-grants-2014_03
Patent number
US08680116B2

Reaction notes

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