Dimethylformamide → 4-Bromo-2-cyclobutoxy-1-methoxymethoxybenzene

HRID 2097463Notes

Reaction equation

CN(C)C=O.[Br:6][C:7]1[CH:8]=[CH:9][C:10]([O:14][CH2:15][O:16][CH3:17])=[C:11]([OH:13])[CH:12]=1.C(=O)([O-])[O-].[K+].[K+].[CH:24]1(Br)[CH2:27][CH2:26][CH2:25]1>O>[Br:6][C:7]1[CH:8]=[CH:9][C:10]([O:14][CH2:15][O:16][CH3:17])=[C:11]([O:13][CH:24]2[CH2:27][CH2:26][CH2:25]2)[CH:12]=1

Participants

Conditions

Temperature: 100 °C

Procedure

To 10 ml of N,N-dimethylformamide solution containing 1.73 g (7.4 mmol) of 5-bromo-2-methoxymethoxyphenol obtained in Reference Example 5-(b) were added 1.0 g (7.2 mmol) of potassium carbonate and 1.0 g (7.4 mmol) of cyclobutyl bromide, and the mixture was stirred at 100° C. for 5 hours. After completion of the reaction, 10 ml of water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer after separation was washed with a saturated aqueous solution of sodium chloride, dried over anhydrous sodium sulfate and then concentrated under reduced pressure. The obtained residue was applied to silica gel column chromatography (Eluent; hexane:ethyl acetate=9:1 (V/V)), and the fractions containing the desired compound were concentrated under reduced pressure to obtain 1.4 g of the title compound as a colorless oil. (Yield: 66%)

Workup

additionwas added to the reaction mixture
extractionthe mixture was extracted with ethyl acetate
customThe organic layer after separation
washwas washed with a saturated aqueous solution of sodium chloride
dry with materialdried over anhydrous sodium sulfate
concentrationconcentrated under reduced pressure
additionthe fractions containing the desired compound
concentrationwere concentrated under reduced pressure

Sources & evidence

ORD record: ord-ff9ca79b9b274449971d161d0a1583de
Source dataset: uspto-grants-2013_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08450319B2

Reaction notes

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