Water → Isohexane ethyl acetate

HRID 2234451Notes

Reaction equation

HRID 2234451 reaction equation
[C:1]([O:5][C:6](=[O:15])[C:7]1[CH:12]=[CH:11][C:10]([NH2:13])=[CH:9][C:8]=1[F:14])([CH3:4])([CH3:3])[CH3:2].[Cl:16]N1C(=O)CCC1=O.O>CN(C=O)C>[C:6]([O:5][CH2:1][CH3:2])(=[O:15])[CH3:7].[CH3:10][CH2:9][CH2:8][CH:7]([CH3:12])[CH3:6].[C:1]([O:5][C:6](=[O:15])[C:7]1[CH:12]=[C:11]([Cl:16])[C:10]([NH2:13])=[CH:9][C:8]=1[F:14])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 3

HCID 962WaterHCID 31398ChlorosuccinimideHCID 10058989Tert-butyl 4-amino-2-fluorobenzoate

Product 2

HCID 21882781Isohexane ethyl acetateYield 5%HCID 68684306Tert-butyl 4-amino-5-chloro-2-fluorobenzoate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

4-Amino-2-fluorobenzoic acid tert-butyl ester (ABChem. Inc.; 1 g, 4.73 mmol) in DMF (15 mL) was added dropwise to N-chlorosuccinimide (633 mg, 4.73 mmol) in DMF (20 mL). The mixture was stirred at room temperature for 72 hours. The reaction mixture was poured into water (130 mL) and extracted with ethyl acetate (2×50 mL). The combined extracts were washed with water, brine, dried (MgSO4) and concentrated. Column chromatography (5% ethyl acetate/isohexane) yielded the title compound as a pale yellow, crystalline solid (321 mg, 27.5%).

Workup

  1. extractionextracted with ethyl acetate (2×50 mL)
  2. washThe combined extracts were washed with water, brine
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-5de0fcd04054423bae9f2ba133d0b7c2
Source dataset
uspto-grants-2010_05
Patent number
US07709471B2

Reaction notes

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