Hydrochloric Acid → HCID 59637316, compound

HRID 2271418Notes

Reaction equation

HRID 2271418 reaction equation
Cl[CH:2]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:3]([O:5][CH2:6][CH3:7])=[O:4].[F:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[N+:21]([O-:23])=[O:22].Cl>CN(C=O)C.O>[F:14][C:15]1[CH:20]=[C:19]([CH:2]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[C:3]([O:5][CH2:6][CH3:7])=[O:4])[CH:18]=[CH:17][C:16]=1[N+:21]([O-:23])=[O:22]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 738951-Fluoro-2-nitrobenzeneHCID 97752Ethyl α-chlorobenzeneacetate

Product 1

HCID 59637316HCID 59637316, compoundYield 44.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
-45 °C

Procedure

9.8 g of potassium tert. butylate were dissolved in 90 ml of DMF and cooled to −45° C. For this purpose, a mix of ethyl 2-chloro-2-phenylacetate (43.8 mmol, 8.7 g) and 1-fluoro-2-nitrobenzene (43.8 mmol, 4.6 ml) was carefully added dropwise and the mixture was stirred for a further 20 minutes. The reaction mix was set to pH 4 using 16% HCl, diluted with 25 ml of water and extracted with EE (3×50 ml). Once combined, the organic phases were washed with water and sat. aq. NaCl sol., dried over MgSO4 and concentrated under vacuum. The residue obtained was purified by column chromatography (silica gel: mesh 100-200, eluent: 10% EE in cyclohexane) and produced 5.9 g (44.9%) of product.

Workup

  1. additionwas carefully added dropwise
  2. additionThe reaction mix
  3. extractionextracted with EE (3×50 ml)
  4. washthe organic phases were washed with water and sat. aq. NaCl sol.
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated under vacuum
  7. customThe residue obtained
  8. customwas purified by column chromatography (silica gel: mesh 100-200, eluent: 10% EE in cyclohexane)

Sources & evidence

ORD record
ord-672c5750038e4fb0bb4077010c0d3c12
Source dataset
uspto-grants-2015_09
Patent number
US09120756B2

Reaction notes

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