Potassium Carbonate → 3-((4-Bromo-3,5-dimethylphenoxy)methyl)tetrahydrofuran

HRID 237439Notes

Reaction equation

[Br:1][C:2]1[C:7]([CH3:8])=[CH:6][C:5]([OH:9])=[CH:4][C:3]=1[CH3:10].C([O-])([O-])=O.[K+].[K+].Br[CH2:18][CH:19]1[CH2:23][CH2:22][O:21][CH2:20]1>CN(C)C=O>[Br:1][C:2]1[C:7]([CH3:8])=[CH:6][C:5]([O:9][CH2:18][CH:19]2[CH2:23][CH2:22][O:21][CH2:20]2)=[CH:4][C:3]=1[CH3:10]

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of 4-bromo-3,5-dimethylphenol (1.5 g) and K2CO3 (3.2 g) in N,N-dimethylformamide (12 mL) is added 3-(bromomethyl)tetrahydrofuran (3.6 g). The mixture is stirred for 16 hours at 80° C. and then partitioned between water and ethyl acetate. The organic phase is washed with brine and dried (MgSO4). The solvent is evaporated and the residue is chromatographed on silica gel (cyclohexane/ethyl acetate 99:1→70:30) to give the title compound. Yield: 1.72 g; LC (method 1): tR=1.37 min; Mass spectrum (ESI+): m/z=285 [M+H]+.

Workup

custompartitioned between water and ethyl acetate
washThe organic phase is washed with brine
dry with materialdried (MgSO4)
customThe solvent is evaporated
customthe residue is chromatographed on silica gel (cyclohexane/ethyl acetate 99:1→70:30)

Sources & evidence

ORD record: ord-ddd2cd0ac111469b85faf23225b365fa
Source dataset: uspto-grants-2014_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08642585B2

Reaction notes

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