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

HRID 566184Notes

Reaction equation

HRID 566184 reaction equation
Cl[C:2]([O:4][CH2:5][CH3:6])=[O:3].[Br:7][C:8]1[C:14]([O:15][CH2:16][CH3:17])=[CH:13][C:11]([NH2:12])=[C:10]([F:18])[CH:9]=1.N1C=CC=CC=1>C(Cl)Cl>[Br:7][C:8]1[C:14]([O:15][CH2:16][CH3:17])=[CH:13][C:11]([NH:12][C:2](=[O:3])[O:4][CH2:5][CH3:6])=[C:10]([F:18])[CH:9]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 10928Ethyl chloroformateHCID 132814294-Bromo-5-ethoxy-2-fluoroaniline

Product 1

HCID 21265588ethyl N-(4-bromo-5-ethoxy-2-fluorophenyl)carbamateYield 96.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
10 °C

Procedure

Ethyl chloroformate (2.15 g) was added dropwise to a solution of 4-bromo-5-ethoxy-2-fluoroaniline (4.21 g) and pyridine (2.84 g) in methylene chloride (36 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, and the resulting crude crystals were crystallized from a mixed solvent of ethyl acetate and n-hexane (1:5 v/v) to obtain the objective ethyl N-(4-bromo-5-ethoxy-2-fluorophenyl)carbamate (5.30 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
  6. customthe resulting crude crystals were crystallized from a mixed solvent of ethyl acetate and n-hexane (1:5 v/v)

Sources & evidence

ORD record
ord-296db66172274adf93bcc36a6c01abf3
Source dataset
uspto-grants-2001_01
Patent number
US06174839B1

Reaction notes

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