Methyl chloroformate → Methyl (2-tert-butyl-4-bromophenyl) carbonate

HRID 1915325Notes

Reaction equation

HRID 1915325 reaction equation
[C:1]([C:5]1[CH:10]=[C:9]([Br:11])[CH:8]=[CH:7][C:6]=1[OH:12])([CH3:4])([CH3:3])[CH3:2].CCN(CC)CC.Cl[C:21]([O:23][CH3:24])=[O:22]>ClCCl>[C:21](=[O:22])([O:12][C:6]1[CH:7]=[CH:8][C:9]([Br:11])=[CH:10][C:5]=1[C:1]([CH3:4])([CH3:2])[CH3:3])[O:23][CH3:24]

Participants

5

Reactant 3

HCID 6586Methyl chloroformateHCID 8471TriethylamineHCID 970684-Bromo-2-tert-butylphenol

Product 1

HCID 57470234Methyl (2-tert-butyl-4-bromophenyl) carbonate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 2-t-butyl-4-bromophenol (380 g, 1.67 mol) in dichloromethane (1000 mL) was added Et3N (202 g, 2 mol) at room temperature. Methyl chloroformate (155 mL) was added dropwise to the above solution at 0° C. After addition, the mixture was stirred at 0° C. for 2 h., quenched with saturated ammonium chloride solution and diluted with water. The organic layer was separated and washed with water and brine, dried over Na2SO4, and concentrated to provide the crude methyl (2-tert-butyl-4-bromophenyl) carbonate (470 g), which was used without further purification.

Workup

  1. additionAfter addition
  2. customquenched with saturated ammonium chloride solution
  3. additiondiluted with water
  4. customThe organic layer was separated
  5. washwashed with water and brine
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-39305253a72a4eee8b39ea215dc29215
Source dataset
uspto-grants-2013_12
Patent number
US08614327B2

Reaction notes

Loading…