Pyridine → Benzyl (2,4-difluorophenyl)carbamate

HRID 1261084Notes

Reaction equation

HRID 1261084 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-d793140415b34b7faebe60bbeca28bb2
Source dataset
uspto-grants-2013_06
Patent number
US08470818B2

Reaction notes

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