Bromide ion → 1-[3-Tert-butyl-5-(3-hydroxy-2,2-dimethylpropoxy)-4-methoxyphenyl]ethanone

HRID 657974Notes

Reaction equation

[C:1]([C:5]1[CH:6]=[C:7]([C:14](=[O:16])[CH3:15])[CH:8]=[C:9]([OH:13])[C:10]=1[O:11][CH3:12])([CH3:4])([CH3:3])[CH3:2].C([O:20][CH2:21][C:22]([CH3:26])([CH3:25])[CH2:23]Br)(=O)C.C(=O)([O-])[O-].[Cs+].[Cs+].[Br-]>CN(C=O)C>[C:1]([C:5]1[CH:6]=[C:7]([C:14](=[O:16])[CH3:15])[CH:8]=[C:9]([O:13][CH2:23][C:22]([CH3:26])([CH3:25])[CH2:21][OH:20])[C:10]=1[O:11][CH3:12])([CH3:4])([CH3:2])[CH3:3]

Participants

Conditions

Temperature: 150 °C

Procedure

1-(3-tert-Butyl-5-hydroxy-4-methoxyphenyl)ethanone (O3.070; 2.00 g) and 3-bromo-2,2-dimethylpropyl acetate (2.54 g) were dissolved in DMF (15 ml), and cesium carbonate (3.69 g) was added. After stirring at 150° C. and max. 15 bar in a microwave for 2.5 h, a further 0.5 eq. of the bromide was added and the mixture was placed into the microwave at 150° C. for a further 2 h. Then the mixture was concentrated by rotary evaporation and the residue was partitioned between DCM and water. The DCM phase was removed, dried over magnesium sulfate, filtered and concentrated. The residue was purified using silica gel (120 g cartridge, n-heptane/MtB ether gradient of 0-50% within 60 min). 1.17 g of the title compound were obtained.

Workup

waitthe mixture was placed into the microwave at 150° C. for a further 2 h
concentrationThen the mixture was concentrated by rotary evaporation
customthe residue was partitioned between DCM and water
customThe DCM phase was removed
dry with materialdried over magnesium sulfate
filtrationfiltered
concentrationconcentrated
customThe residue was purified
customsilica gel (120 g cartridge, n-heptane/MtB ether gradient of 0-50% within 60 min)

Sources & evidence

ORD record: ord-5886e22312b8419aa10f0ec847f42304
Source dataset: uspto-grants-2011_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08076336B2

Reaction notes

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