Chlorosuccinimide → tert-Butyl 1-(5-amino-2-chloro-4-fluorobenzyl)cyclopropanecarboxylate

HRID 1475622Notes

Reaction equation

HRID 1475622 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:16]=[CH:17][C:18]=1[F:19])[CH2:5][C:6]1([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:8][CH2:7]1.[Cl:20]N1C(=O)CCC1=O>C(#N)C>[NH2:1][C:2]1[C:18]([F:19])=[CH:17][C:16]([Cl:20])=[C:4]([CH:3]=1)[CH2:5][C:6]1([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:7][CH2:8]1

Participants

4

Reactant 2

HCID 31398ChlorosuccinimideHCID 58136688tert-Butyl 1-(3-amino-4-fluorobenzyl)cyclopropanecarboxylate

Product 1

HCID 68006954tert-Butyl 1-(5-amino-2-chloro-4-fluorobenzyl)cyclopropanecarboxylate

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

2.0 g (7.54 mmol) of tert-butyl 1-(3-amino-4-fluorobenzyl)cyclopropanecarboxylate were dissolved in 20.0 ml of acetonitrile, and 1.06 g (7.92 mmol) of N-chlorosuccinimide were added in several portions at RT. The reaction mixture was stirred at RT for 80 min and then at 45° C. for 8 h. After cooling, the acetonitrile was removed under reduced pressure. The residue was taken up in dichloromethane and washed with saturated sodium bicarbonate solution and saturated sodium chloride solution. The organic phase was dried over sodium sulphate and concentrated under reduced pressure. By chromatography on silica gel (mobile phase cyclohexane/ethyl acetate 30:1) 1.41 g (62.3% of theory) of the title compound were isolated from the crude product obtained in this manner.

Workup

  1. waitat 45° C. for 8 h
  2. temperatureAfter cooling
  3. customthe acetonitrile was removed under reduced pressure
  4. washwashed with saturated sodium bicarbonate solution and saturated sodium chloride solution
  5. dry with materialThe organic phase was dried over sodium sulphate
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-e961560208724c1b8ea8d270f16b20e3
Source dataset
uspto-grants-2015_04
Patent number
US09018258B2

Reaction notes

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