Pyridine → Methyl (3,5-dibromo-4-fluorophenyl)carbamate
Reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:6]=[C:7]([Br:10])[C:8]=1[F:9])[NH2:5].N1C=CC=CC=1.Cl[C:18]([O:20][CH3:21])=[O:19]>C(Cl)Cl>[Br:1][C:2]1[CH:3]=[C:4]([NH:5][C:18](=[O:19])[O:20][CH3:21])[CH:6]=[C:7]([Br:10])[C:8]=1[F:9]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 2.5 °C
Procedure
3,5-dibromo-4-fluoroaniline (1.6 g, 4.16 mmol) was dissolved in DCM (41.6 ml). Pyridine (0.90 ml, 11.13 mmol) was added and the reaction mixture cooled to 0-5° C. Methyl chloroformate (0.66 ml, 8.52 mmol) was added drop wise via syringe. The reaction mixture was stirred at 0-5° C. for 1 hour. The reaction mixture was diluted with additional 50 ml dichloromethane and washed with 0.5 M citric acid twice, NaHCO3 solution once and brine once, then dried over MgSO4, filtered and evaporated to dryness. Chromatography on silica (gradient from 100% hexanes to 100% DCM) gave methyl (3,5-dibromo-4-fluorophenyl)carbamate (1.22 g) as a colorless fluffy solid.
Workup
- washwashed with 0.5 M citric acid twice
- dry with materialNaHCO3 solution once and brine once, then dried over MgSO4
- filtrationfiltered
- customevaporated to dryness
Sources & evidence
- ORD record
- ord-36867c84b98b46a8aad11483c3b890c4
- Source dataset
- uspto-grants-2016_03
- Patent number
- US09273057B2
Reaction notes
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