Pyridine → ethyl N-(5-allyloxy-4-bromo-2-fluorophenyl)carbamate

HRID 566194Notes

Reaction equation

HRID 566194 reaction equation
Cl[C:2]([O:4][CH2:5][CH3:6])=[O:3].[CH2:7]([O:10][C:11]1[C:12]([Br:19])=[CH:13][C:14]([F:18])=[C:15]([CH:17]=1)[NH2:16])[CH:8]=[CH2:9].N1C=CC=CC=1>C(Cl)Cl>[CH2:7]([O:10][C:11]1[C:12]([Br:19])=[CH:13][C:14]([F:18])=[C:15]([NH:16][C:2](=[O:3])[O:4][CH2:5][CH3:6])[CH:17]=1)[CH:8]=[CH2:9]

Participants

5

Reactant 3

HCID 1049PyridineHCID 10928Ethyl chloroformateHCID 212655985-Allyloxy-4-bromo-2-fluoroaniline

Product 1

HCID 21265559ethyl N-(5-allyloxy-4-bromo-2-fluorophenyl)carbamateYield 98.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
10 °C

Procedure

Ethyl chloroformate (5.97 g) was added dropwise to a solution of 5-allyloxy-4-bromo-2-fluoroaniline (12.3 g) and pyridine (7.90 g) in methylene chloride (100 ml) at 0° C., and the mixture was stirred at 10° C. for 3 hours. After the reaction, this was extracted with methylene chloride, then washed with diluted hydrochloric acid and an aqueous sodium hydrogencarbonate solution, and dried over anhydrous magnesium sulfate. Then, methylene chloride was distilled off to obtain to the objective ethyl N-(5-allyloxy-4-bromo-2-fluorophenyl)carbamate (15.67 g).

Workup

  1. customAfter the reaction
  2. extractionthis was extracted with methylene chloride
  3. washwashed with diluted hydrochloric acid
  4. dry with materialan aqueous sodium hydrogencarbonate solution, and dried over anhydrous magnesium sulfate
  5. distillationThen, methylene chloride was distilled off

Sources & evidence

ORD record
ord-fc87c21c7daf4bdfac9311e38a6a25ec
Source dataset
uspto-grants-2001_01
Patent number
US06174839B1

Reaction notes

Loading…