Pyridine → HCID 2166334, compound

HRID 566190Notes

Reaction equation

HRID 566190 reaction equation
Cl[C:2]([O:4][CH2:5][CH3:6])=[O:3].[Br:7][C:8]1[CH:14]=[CH:13][C:11]([NH2:12])=[C:10]([F:15])[CH:9]=1.N1C=CC=CC=1>C(Cl)Cl>[Br:7][C:8]1[CH:14]=[CH:13][C:11]([NH:12][C:2](=[O:3])[O:4][CH2:5][CH3:6])=[C:10]([F:15])[CH:9]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 10928Ethyl chloroformateHCID 1230504-Bromo-2-fluoroaniline

Product 1

HCID 2166334HCID 2166334, compoundYield 98.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
10 °C

Procedure

Ethyl chloroformate (15.91 g) was added dropwise to a solution of 4-bromo-2-fluoroaniline (25.33 g) and pyridine (21.06 g) in methylene chloride (260 ml) at 0° C., and the mixture was stirred at 10° C. for 3 hours. After the reaction, it 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 ethyl acetate-n-hexane (1:5 v/v) to obtain the objective ethyl N-(4-bromo-2-fluorophenyl)carbamate (34.45 g).

Workup

  1. customAfter the reaction, it
  2. extractionwas 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 ethyl acetate-n-hexane (1:5 v/v)

Sources & evidence

ORD record
ord-6b644217c4024409ab2f48ba7aa6c90a
Source dataset
uspto-grants-2001_01
Patent number
US06174839B1

Reaction notes

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