Dimethylformamide → HCID 131726197, compound

HRID 1373249Notes

Reaction equation

HRID 1373249 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[C:4](F)[CH:3]=1.[OH:12][C:13]1[CH:14]=[C:15]([C@H:19]([NH:21][C:22](=[O:28])[O:23][C:24]([CH3:27])([CH3:26])[CH3:25])[CH3:20])[CH:16]=[CH:17][CH:18]=1.C(=O)([O-])[O-].[K+].[K+].CN(C)C=O>O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[C:4]([CH:3]=1)[O:12][C:13]1[CH:14]=[C:15]([C@H:19]([NH:21][C:22](=[O:28])[O:23][C:24]([CH3:27])([CH3:26])[CH3:25])[CH3:20])[CH:16]=[CH:17][CH:18]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 696914-Chloro-2-fluoro-1-nitrobenzeneHCID 56955758HCID 56955758, compound

Product 1

HCID 131726197HCID 131726197, compoundYield 60.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 4-chloro-2-fluoronitrobenzene (10.6 g, 54 mmols), tert-butyl(1R)-1-(3-hydroxyphenyl)ethylcarbamate (13.7 g, 58 mmols), potassium carbonate (8.7 g, 63 mmols) and N,N-dimethylformamide (150 ml) was stirred at 100° C. for 1 hour. The reaction mixture was cooled, poured into water, and extracted with ethyl acetate. The extract was washed with water and brine, and then dried with anhydrous magnesium sulfate, and the solvent was evaporated away. The residue was purified through silica gel column chromatography, and the resulting crystal was re-crystallized from hexane/ethyl acetate to give a crystal of tert-butyl(1R)-(-)-1-[3-(5-chloro-2-nitrophenoxy)phenyl]ethylcarbamate (12.9 g, 60%).

Workup

  1. temperatureThe reaction mixture was cooled
  2. extractionextracted with ethyl acetate
  3. washThe extract was washed with water and brine
  4. dry with materialdried with anhydrous magnesium sulfate
  5. customthe solvent was evaporated away
  6. customThe residue was purified through silica gel column chromatography
  7. customthe resulting crystal was re-crystallized from hexane/ethyl acetate

Sources & evidence

ORD record
ord-22f73ec8a879476d957cde3a14e70b1d
Source dataset
uspto-grants-2007_01
Patent number
US07160887B1

Reaction notes

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