N-bromobutanimide → HCID 18451498, compound

HRID 1270736Notes

Reaction equation

HRID 1270736 reaction equation
[Cl:1][C:2]1[CH:8]=[CH:7][C:6]([CH:9]2[CH2:11][CH2:10]2)=[C:5]([F:12])[C:3]=1[NH2:4].[Br:13]N1C(=O)CCC1=O>CN(C=O)C>[Cl:1][C:2]1[CH:8]=[C:7]([Br:13])[C:6]([CH:9]2[CH2:10][CH2:11]2)=[C:5]([F:12])[C:3]=1[NH2:4]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 18451507HCID 18451507, compound

Product 1

HCID 18451498HCID 18451498, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2-Chloro-5-cyclopropyl-6-fluoroaniline (9.4 g, 50.6 mmol) and N-bromosuccinimide (9.4 g, 52.8 mmol) are dissolved with stirring in 100 mL of anhydrous DMF. The reaction mixture is stirred overnight and then most of the DMF is removed by rotary evaporator under high vacuum. The residue is partitioned between 1:1 Et2O/hexane (500 mL) and water (500 mL). The organic layer is washed with brine (3×250 mL), dried (MgSO4) and concentrated by rotary evaporator. The crude material is purified using flash chromatography (7% CH2Cl2/hexanes) to give 2-chloro-4-bromo-5-cyclopropyl-6-fluoroaniline as a light orange oil.

Workup

  1. custommost of the DMF is removed by rotary evaporator under high vacuum
  2. customThe residue is partitioned between 1:1 Et2O/hexane (500 mL) and water (500 mL)
  3. washThe organic layer is washed with brine (3×250 mL)
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated by rotary evaporator
  6. customThe crude material is purified

Sources & evidence

ORD record
ord-44a1c720c55a4e719bf404755c04441a
Source dataset
uspto-grants-2007_04
Patent number
US07202364B2

Reaction notes

Loading…