Hydrochloric Acid → HCID 59637336, compound

HRID 1842861Notes

Reaction equation

HRID 1842861 reaction equation
Cl[CH:2]([CH:8]1[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]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>[CH:8]1([CH:2]([C:19]2[CH:18]=[CH:17][C:16]([N+:21]([O-:23])=[O:22])=[C:15]([F:14])[CH:20]=2)[C:3]([O:5][CH2:6][CH3:7])=[O:4])[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 738951-Fluoro-2-nitrobenzeneHCID 13215910HCID 13215910, compound

Product 1

HCID 59637336HCID 59637336, compoundYield 49%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
-45 °C

Procedure

8.2 g of potassium tert.butylate were dissolved in 70 ml of DMF and cooled to −45° C. For this purpose, a mix of ethyl 2-chloro-2-cyclohexylacetate (36.6 mmol, 7.5 g) and 1-fluoro-2-nitrobenzene (36.6 mmol, 3.9 ml) was carefully added dropwise and 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 EtOAc (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 resulting residue was purified by column chromatography (silica gel: mesh 100-200, eluent: 10% EtOAc in cyclohexane) and produced 5.5 g (49%) of product.

Workup

  1. additionwas carefully added dropwise
  2. additionThe reaction mix
  3. extractionextracted with EtOAc (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 resulting residue was purified by column chromatography (silica gel: mesh 100-200, eluent: 10% EtOAc in cyclohexane)

Sources & evidence

ORD record
ord-38817994863b4e16b0c3ffa8aab63b5d
Source dataset
uspto-grants-2015_02
Patent number
US08946204B2

Reaction notes

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