Methyl chloroformate → Methyl[2-(2-bromophenyl)ethyl]carbamate

HRID 387657Notes

Reaction equation

HRID 387657 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][CH2:9][NH2:10].C(=O)([O-])[O-].[K+].[K+].[C:17](Cl)(=[O:20])[O:18][CH3:19]>O1CCCC1>[CH3:19][O:18][C:17](=[O:20])[NH:10][CH2:9][CH2:8][C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[Br:1]

Participants

5

Reactant 3

HCID 6586Methyl chloroformateHCID 11430Potassium CarbonateHCID 27340912-Bromophenethylamine

Product 1

HCID 59401358Methyl[2-(2-bromophenyl)ethyl]carbamate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

5 g of 2-(2-bromophenyl)ethanamine and 10 g of potassium carbonate in 30 cm3 of anhydrous tetrahydrofuran are stirred under an inert atmosphere at a temperature close to 10° C. 2.5 cm3 of methyl chlorocarbonate in solution in 10 cm3 of tetrahydrofuran are poured into the reaction mixture. After returning to a temperature close to 20° C., the reaction mixture is heated for 2 h at the reflux of the solvent. The potassium carbonate is filtered and washed with tetrahydrofuran. The filtrate is concentrated using a rotary evaporator under reduced pressure (5 kPa). 3.43 g of methyl[2-(2-bromophenyl)ethyl]carbamate are obtained in the form of a colorless thick oil

Workup

  1. customclose to 10° C
  2. customclose to 20° C.
  3. temperaturethe reaction mixture is heated for 2 h at the
  4. temperaturereflux of the solvent
  5. filtrationThe potassium carbonate is filtered
  6. washwashed with tetrahydrofuran
  7. concentrationThe filtrate is concentrated
  8. customa rotary evaporator under reduced pressure (5 kPa)

Sources & evidence

ORD record
ord-81a595efa3224c76bcf90a4efefab9cb
Source dataset
uspto-grants-2013_02
Patent number
US08372864B2

Reaction notes

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