Methyl chloroformate → Methyl (4-bromo-3-methylphenyl)carbamate

HRID 853094Notes

Reaction equation

HRID 853094 reaction equation
[Br:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][C:3]=1[CH3:9].C(=O)(O)[O-].[Na+].Cl[C:16]([O:18][CH3:19])=[O:17]>ClCCl.O>[CH3:19][O:18][C:16](=[O:17])[NH:6][C:5]1[CH:7]=[CH:8][C:2]([Br:1])=[C:3]([CH3:9])[CH:4]=1

Participants

6

Reactant 3

HCID 6586Methyl chloroformateHCID 233594-Bromo-3-methylanilineHCID 516892Sodium Bicarbonate

Product 1

HCID 28378453Methyl (4-bromo-3-methylphenyl)carbamateYield 98.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 10.00 g 4-bromo-3-methylaniline in 50 ml dichloromethane was added 80 ml of a 10% solution of sodium bicarbonate in water. The mixture was cooled to 0° C. and 6.2 ml (7.62 g) methyl chloroformate was added during 10 min. with stirring. The reaction mixture was stirred at room temperature for 1 h. The phases were separated. The organic phase was washed with a 10% solution of citric acid in water, 10% solution of sodium bicarbonate in water and brine, dried with magnesium sulfate and evaporated to yield 12.94 g of (4-bromo-3-methyl-phenyl)-carbamic acid methyl ester as light brown solid melting at 71–72° C.

Workup

  1. stirringThe reaction mixture was stirred at room temperature for 1 h
  2. customThe phases were separated
  3. washThe organic phase was washed with a 10% solution of citric acid in water, 10% solution of sodium bicarbonate in water and brine
  4. dry with materialdried with magnesium sulfate
  5. customevaporated

Sources & evidence

ORD record
ord-2f4b7b1ba86f4b18a3d9705324b35676
Source dataset
uspto-grants-2007_08
Patent number
US07253281B2

Reaction notes

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