Hydrochloric Acid → HCID 59637336, compound

HRID 2271415Notes

Reaction equation

HRID 2271415 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 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 5.5 g (49%) 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-d7b3829d4d1d4d5baa3d0f3f34f7746b
Source dataset
uspto-grants-2015_09
Patent number
US09120756B2

Reaction notes

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