Pyridine → Benzyl (2,4-difluorophenyl)carbamate

HRID 250628Notes

Reaction equation

HRID 250628 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[NH2:9].N1C=CC=CC=1.Cl[C:17]([O:19][CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)=[O:18]>ClCCl>[CH2:20]([O:19][C:17](=[O:18])[NH:9][C:3]1[CH:4]=[CH:5][C:6]([F:8])=[CH:7][C:2]=1[F:1])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 97092,4-DifluoroanilineHCID 10387Benzyl chloroformate

Product 1

HCID 11954520Benzyl (2,4-difluorophenyl)carbamateYield 85%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To 2,4-difluoroaniline (42, 7.0 mL, 0.070 mol) in 100 mL of dichloromethane was added pyridine (11 mL, 0.14 mol) and benzyl chloroformate (11.9 mL, 0.0834 mol). The reaction mixture was stirred at ambient temperature for 1.5 hours. The reaction mixture was concentrated under reduced pressure and the residue was partitioned between ethyl acetate and KHSO4 solution. The organic layer was dried (MgSO4), concentrated and crystallized from hexanes to give compound 613 (15.6 g, 85%).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customthe residue was partitioned between ethyl acetate and KHSO4 solution
  3. dry with materialThe organic layer was dried (MgSO4)
  4. concentrationconcentrated
  5. customcrystallized from hexanes

Sources & evidence

ORD record
ord-99134354ed644ea299e65bca3ddd0861
Source dataset
uspto-grants-2011_01
Patent number
US07863288B2

Reaction notes

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