Hydrochloric Acid → HCID 59637336, compound

HRID 1027966Notes

Reaction equation

CC([O-])(C)C.[K+].Cl[CH:8]([CH:14]1[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]1)[C:9]([O:11][CH2:12][CH3:13])=[O:10].[F:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=1[N+:27]([O-:29])=[O:28].Cl>CN(C=O)C.O>[CH:14]1([CH:8]([C:25]2[CH:24]=[CH:23][C:22]([N+:27]([O-:29])=[O:28])=[C:21]([F:20])[CH:26]=2)[C:9]([O:11][CH2:12][CH3:13])=[O:10])[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]1

Participants

Conditions

Temperature: -45 °C

Procedure

8.2 g of potassium tert-butylate were dissolved in 70 mL of DMF and cooled to −45° C. To this, a mixture of ethyl 2-chloro-2-cyclohexylacetate (36.6 mmol, 7.5 g) and 1-fluoro-2-nitrobenzene (36.6 mmol, 3.9 mL) was gently added dropwise and stirring was continued for a further 20 minutes. The reaction mixture was set to pH 4 with 16% strength aq. HCl, diluted with 25 mL of water, and extracted with EA (3×50 mL). After combining the organic phases, they were washed with water and sat. aq. NaCl solution, dried over MgSO4, and concentrated in vacuo. The resulting residue was purified by column chromatography (silica gel: mesh 100-200, eluent: 10% EA in cyclohexane) and yielded 5.5 g (49%) of the desired product.

Workup

additionwas gently added dropwise
extractionextracted with EA (3×50 mL)
washwere washed with water and sat. aq. NaCl solution
dry with materialdried over MgSO4
concentrationconcentrated in vacuo
customThe resulting residue was purified by column chromatography (silica gel: mesh 100-200, eluent: 10% EA in cyclohexane)

Sources & evidence

ORD record: ord-e74e165738674d408b9ffec3e4d7135a
Source dataset: uspto-grants-2014_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08735426B2

Reaction notes

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