Hydrochloric Acid → HCID 22312896, compound

HRID 984042Notes

Reaction equation

[H-].[Na+].[Cl:3][C:4]1[CH:9]=[CH:8][C:7]([CH2:10][C:11]#[N:12])=[CH:6][CH:5]=1.[Br:13][C:14]1[CH:19]=[C:18]([N+:20]([O-:22])=[O:21])[CH:17]=[C:16]([Br:23])[C:15]=1OC.Cl>CN(C=O)C.O>[Br:13][C:14]1[CH:19]=[C:18]([N+:20]([O-:22])=[O:21])[CH:17]=[C:16]([Br:23])[C:15]=1[CH:10]([C:7]1[CH:8]=[CH:9][C:4]([Cl:3])=[CH:5][CH:6]=1)[C:11]#[N:12]

Participants

Conditions

Temperature: 0 °C

Procedure

NaH (0.0772 mol) was added portionwise at 0° C. under N2 flow to a mixture of 4-chloro-benzeneacetonitrile (0.0643 mol) in DMF (50 ml). The mixture was stirred at 0° C. under N2 flow for 1 hour. A mixture of 1,3-dibromo-2-methoxy-5-nitro-benzene (0.0643 mol) in DMF (50 ml) was added at 0° C. under N2 flow. The mixture was stirred at RT for 3 hours, hydrolized with H2O and HCl 3N and extracted with EtOAc. The organic layer was separated, dried, filtered and the solvent was evaporated. The residue was purified by column chromatography over silica gel (eluent: CH2Cl2/cyclohexane 60/40). The pure fractions were collected and the solvent was evaporated, yielding 12.8 g (46%) of (±)-2,6-dibromo-α-(4-chlorophenyl)-4-nitrobenzeneacetonitrile (interm. 76).

Workup

additionwas added at 0° C. under N2 flow
extractionextracted with EtOAc
customThe organic layer was separated
customdried
filtrationfiltered
customthe solvent was evaporated
customThe residue was purified by column chromatography over silica gel (eluent: CH2Cl2/cyclohexane 60/40)
customThe pure fractions were collected
customthe solvent was evaporated

Sources & evidence

ORD record: ord-a3fa5d9219814adf95b48e0b86662397
Source dataset: uspto-grants-2005_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06867207B2

Reaction notes

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