Benzene → tert-butyl 2-[4-(1H-imidazol-1-yl)phenyl]ethylcarbamate

HRID 1071969Notes

Reaction equation

HRID 1071969 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][NH:10][C:11](=[O:17])[O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[CH:4][CH:3]=1.[NH:18]1[CH:22]=[CH:21][N:20]=[CH:19]1.C1C=CC=CC=1.N1C2C(=CC=C3C=2N=CC=C3)C=CC=1.C([O-])([O-])=O.[Cs+].[Cs+]>O.CC1C=CC=CC=1C>[N:18]1([C:2]2[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][NH:10][C:11](=[O:17])[O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[CH:4][CH:3]=2)[CH:22]=[CH:21][N:20]=[CH:19]1

Participants

8

Reactant 5

HCID 241BenzeneHCID 795ImidazoleHCID 13181,10-PhenanthrolineHCID 10796Cesium carbonateHCID 14221818[2-(4-Bromo-phenyl)ethyl]-carbamic acid tert-butyl ester

Product 1

HCID 22390721tert-butyl 2-[4-(1H-imidazol-1-yl)phenyl]ethylcarbamate

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 7237O-XyleneSolvent

Conditions

Temperature
120 °C

Procedure

Tert-butyl 2-(4-bromophenyl)ethylcarbamate (500 mg, 1.67 mmol), imidazole (170 mg, 2.50 mmol), (CuOTf)2.PhH (84 mg, 0.17 mmol), 1,10-Phenanthroline (360 mg, 2.00 mmol), dba (39 mg, 0.17 mmol), and Cs2CO3 (650 mg, 1.99 mmol) were mixed together in a flask and o-xylene (10 mL) was added. Resulting solution was heated to 120° C. and stirred for four days. Reaction mixture was then cooled, poured into water (20 mL) and extracted with EtOAc (3×20 mL). Combined organics were washed with water (1×20 mL) and brine (2×20 mL), dried over sodium sulfate, filtered, and concentrated Crude product was purified by flash chromatography eluting with 25% Hexanes in EtOAC to pure EtOAc to give tert-butyl 2-[4-(1H-imidazol-1-yl)phenyl]ethylcarbamate.

Workup

  1. customReaction mixture
  2. temperaturewas then cooled
  3. extractionextracted with EtOAc (3×20 mL)
  4. washCombined organics were washed with water (1×20 mL) and brine (2×20 mL)
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated Crude product
  8. customwas purified by flash chromatography
  9. washeluting with 25% Hexanes in EtOAC to pure EtOAc

Sources & evidence

ORD record
ord-7ea792682b45492ea8ca48f40ec1893d
Source dataset
uspto-grants-2005_06
Patent number
US06908921B2

Reaction notes

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