Hydrochloric Acid → HCID 59637316, compound

HRID 1027969Notes

Reaction equation

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

Participants

Conditions

Temperature: -45 °C

Procedure

9.8 g of potassium tert-butylate were dissolved in 90 mL of DMF and cooled to −45° C. To this, a mixture of ethyl 2-chloro-2-phenylacetate (43.8 mmol, 8.7 g) and 1-fluoro-2-nitrobenzene (43.8 mmol, 4.6 mL) was gently added dropwise and stirring was continued for a further 20 minutes. The reaction mixture was set to pH 4 with aq. 16% strength. HCl, diluted with 25 mL of water, and extracted with EA (3×50 mL). Following combination of 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 5.9 g (44.9%) 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-4aa9740996db4975bc4e04773757726e
Source dataset: uspto-grants-2014_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08735426B2

Reaction notes

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