Benzyl chloroformate → N-(4-bromo-3-fluorophenyl)carbamic acid phenylmethyl ester

HRID 2193543Notes

Reaction equation

HRID 2193543 reaction equation
[Br:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][C:3]=1[F:9].C(=O)(O)[O-].[Na+].Cl[C:16]([O:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)=[O:17]>CC(C)=O>[CH2:19]([O:18][C:16](=[O:17])[NH:6][C:5]1[CH:7]=[CH:8][C:2]([Br:1])=[C:3]([F:9])[CH:4]=1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

5

Reactant 3

HCID 10387Benzyl chloroformateHCID 516892Sodium BicarbonateHCID 8218484-Bromo-3-fluoroaniline

Product 1

HCID 67274244N-(4-bromo-3-fluorophenyl)carbamic acid phenylmethyl ester

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of 10 g of 4-bromo-3-fluoroaniline (52 mmol) in 300 ml acetone were added successively 150 ml of a saturated sodium bicarbonate solution and at 0° C. 9 ml of benzyl chloroformate (63 mmol). The reaction was monitored by TLC. The acetone was evaporated, the residue extracted twice with ethyl acetate, washed with water and brine, dried and evaporated. The residue was crystallized from an ethyl acetate/hexane mixture.

Workup

  1. customat 0° C
  2. customThe acetone was evaporated
  3. extractionthe residue extracted twice with ethyl acetate
  4. washwashed with water and brine
  5. customdried
  6. customevaporated
  7. customThe residue was crystallized from an ethyl acetate/hexane mixture

Sources & evidence

ORD record
ord-d33919066faf4b3090ae02d3334d0072
Source dataset
uspto-grants-2012_12
Patent number
US08329908B2

Reaction notes

Loading…