1-Bromo-2-methylpropane → 5-(4-Ethoxy-2-isobutoxy-3-methoxyphenyl)isobenzofuran-1(3H)-one

HRID 2171135Notes

Reaction equation

[CH2:1]([O:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[CH:11]=[C:12]3[C:16](=[CH:17][CH:18]=2)[C:15](=[O:19])[O:14][CH2:13]3)=[C:6]([OH:20])[C:5]=1[O:21][CH3:22])[CH3:2].C(=O)([O-])[O-].[K+].[K+].[CH2:29](Br)[CH:30]([CH3:32])[CH3:31]>C(#N)C>[CH2:1]([O:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[CH:11]=[C:12]3[C:16](=[CH:17][CH:18]=2)[C:15](=[O:19])[O:14][CH2:13]3)=[C:6]([O:20][CH2:29][CH:30]([CH3:32])[CH3:31])[C:5]=1[O:21][CH3:22])[CH3:2]

Participants

Conditions

Temperature: 80 °C

Procedure

To a stirring solution of 5-(4-ethoxy-2-hydroxy-3-methoxyphenyl)isobenzofuran-1(3H)-one (80 mg, 0.266 mmol) in acetonitrile was added potassium carbonate (110 mg, 0.798 mmol) and isobutyl bromide (146 mg, 1.064 mmol) and the resultant reaction mixture was heated to 80° C. for 2 h. The reaction mixture was cooled to RT, filtered through celite and the filtrate was concentrated under reduced pressure. Purification of the residue by flash column chromatography (silica gel, 0-20% ethyl acetate in pet ether) afforded the title compound as a solid (20 mg, 21%).

Workup

customthe resultant reaction mixture
temperatureThe reaction mixture was cooled to RT
filtrationfiltered through celite
concentrationthe filtrate was concentrated under reduced pressure
customPurification of the residue by flash column chromatography (silica gel, 0-20% ethyl acetate in pet ether)

Sources & evidence

ORD record: ord-b685be993e8143acbf84c462734b9b42
Source dataset: uspto-grants-2015_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09051290B2

Reaction notes

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