Water → HCID 67326141, compound

HRID 1029037Notes

Reaction equation

HRID 1029037 reaction equation
Cl([O-])(=O)(=O)=O.[Li+].[O:7]1[C:9]([CH3:11])([CH3:10])[CH2:8]1.[Br:12][C:13]1[C:19]([CH3:20])=[CH:18][CH:17]=[CH:16][C:14]=1[NH2:15].O>C(OCC)C>[Br:12][C:13]1[C:19]([CH3:20])=[CH:18][CH:17]=[CH:16][C:14]=1[NH:15][CH2:8][C:9]([CH3:11])([OH:7])[CH3:10]

Participants

6

Reactant 4

HCID 962WaterHCID 11208Isobutylene oxideHCID 6037812-Bromo-3-methylanilineHCID 23665649Lithium perchlorate

Product 1

HCID 67326141HCID 67326141, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a solution of lithium perchlorate (2.13 g, 20 mmol) in diethyl ether (4 mL) was added 1,2-epoxy-2-methylpropane (0.195 mL, 2.2 mmol), followed by 2-bromo-3-methylaniline (0.250 mL, 2 mmol) under an atmosphere of nitrogen gas. The reaction mixture was stirred overnight at RT. Water was added dropwise, and the product was extracted from the reaction mixture with DCM. The organic phase was dried over MgSO4. The solvent was removed under reduced pressure and the remaining residue was purified by flash chromatography (10-40% hexanes/EtOAc). 1-(2-bromo-3-methylphenylamino)-2-methylpropan-2-ol was obtained as a clear colorless oil.

Workup

  1. extractionthe product was extracted from the reaction mixture with DCM
  2. dry with materialThe organic phase was dried over MgSO4
  3. customThe solvent was removed under reduced pressure
  4. customthe remaining residue was purified by flash chromatography (10-40% hexanes/EtOAc)

Sources & evidence

ORD record
ord-a2c5404529224c40897ecd0c777dc70f
Source dataset
uspto-grants-2014_05
Patent number
US08735384B2

Reaction notes

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