Epibromohydrin → HCID 86729263, compound

HRID 1399856Notes

Reaction equation

HRID 1399856 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([NH:8][C:9](=[O:15])[O:10][C:11]([CH3:14])([CH3:13])[CH3:12])[CH:5]=[CH:6][CH:7]=1.[H-].[Na+].Br[CH2:19][CH:20]1[CH2:22][O:21]1>CN(C=O)C>[O:21]1[CH2:22][CH:20]1[CH2:19][O:1][C:2]1[CH:3]=[C:4]([NH:8][C:9](=[O:15])[O:10][C:11]([CH3:12])([CH3:14])[CH3:13])[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 18430EpibromohydrinHCID 24758Sodium hydrideHCID 312485tert-butyl N-(3-hydroxyphenyl)carbamate

Product 1

HCID 86729263HCID 86729263, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of tert-butyl (3-hydroxyphenyl)carbamate (1 g, 4.79 mmol) in DMF (15 mL) was added NaH (0.126 g, 5.26 mmol) at 0° C. After stirring for 30 min, 2-(bromomethyl)oxirane (0.716 g, 5.26 mmol) was added and the mixture stirred at 0° C. for 1 h before quenching with the addition of MeOH. After evaporation of this mixture, the resulting residue was dissolved in ethyl acetate and washed with water, dried and with sodium sulfate and concentrated with the resulting crude product used for next step without further purification.

Workup

  1. stirringthe mixture stirred at 0° C. for 1 h
  2. custombefore quenching with the addition of MeOH
  3. customAfter evaporation of this mixture
  4. dissolutionthe resulting residue was dissolved in ethyl acetate
  5. washwashed with water
  6. dry with materialdried and with sodium sulfate
  7. concentrationconcentrated with the resulting crude product
  8. customused for next step without further purification

Sources & evidence

ORD record
ord-f36794b6338f4da7a14cca42e3dcc870
Source dataset
uspto-grants-2014_12
Patent number
US08906900B2

Reaction notes

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