Ethyl Acetate → HCID 68670137, compound

HRID 2071044Notes

Reaction equation

Br[C:2]1[CH:7]=[C:6]([C:8]([CH3:10])=[CH2:9])[CH:5]=[C:4]([S:11]([CH:14]([CH3:16])[CH3:15])(=[O:13])=O)[CH:3]=1.[C:17](OCC)(=O)C.[NH4+:23].[OH-:24]>CN(C=O)C.[C-]#N.[C-]#N.[Zn+2].C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH:14]([S:11]([C:4]1[CH:3]=[C:2]([CH:7]=[C:6]([C:8]([CH3:10])=[CH2:9])[CH:5]=1)[C:17]#[N:23])(=[O:13])=[O:24])([CH3:16])[CH3:15]

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of 32 mg (0.106 mmol) of 1-bromo-3-(isopropylsulfonyl)-5-(prop-1-en-2-yl)benzene, 11.2 mmol (0.0954 mmol) of Zn(CN)2 and 24.3 mg of (0.021 mmol) of Pd(PPh3)4 in 3 mL of DMF (degassed) was heated at 100° C. Over a period of 2.5 h, a total of 103 mg of Pd(PPh3)4 was added in 3 portions. Ethyl acetate and 10% NH4OH solution were added, and the organic layer was washed with H2O and brine. The aqueous layer was extracted with EtOAc (3×), and the combined extracts were dried over Na2SO4, filtered, and concentrated. Purification by flash silica gel chromatography (30% EtOAc/hexanes) provided 28.6 mg of 3-(isopropylsulfonyl)-5-(prop-1-en-2-yl)benzonitrile as a yellow solid.

Workup

washthe organic layer was washed with H2O and brine
extractionThe aqueous layer was extracted with EtOAc (3×)
dry with materialthe combined extracts were dried over Na2SO4
filtrationfiltered
concentrationconcentrated
customPurification by flash silica gel chromatography (30% EtOAc/hexanes)

Sources & evidence

ORD record: ord-44c7925375504d97b455b65b346d25dd
Source dataset: uspto-grants-2012_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08299267B2

Reaction notes

Loading…