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

HRID 237435Notes

Reaction equation

HRID 237435 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][C:19]1([CH3:23])[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][C:19]2([CH3:23])[CH2:22][O:21][CH2:20]2)=[CH:4][C:3]=1[CH3:10]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 819704-Bromo-3,5-dimethylphenolHCID 144860Oxetane, 3-(bromomethyl)-3-methyl-

Product 1

HCID 866971023-((4-Bromo-3,5-dimethylphenoxy)methyl)-3-methyloxetane

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 4-bromo-3,5-dimethylphenol (3.0 g) and K2CO3 (5.5 g) in N,N-dimethylformamide (10 mL) is added 3-(bromomethyl)-3-methyloxetane (2.95 g). The mixture is stirred for 12 hours at room temperature and then partitioned between saturated aqueous NaHCO3 solution and ethyl acetate. The aqueous phase is extracted with ethyl acetate and the combined organic phases are dried (MgSO4). The solvent is evaporated and the residue is chromatographed on silica gel (cyclohexane/ethyl acetate 100:0→70:30) to give the title compound. Yield: 3.5 g; LC (method 4): tR=1.81 min; Mass spectrum (ESI+): m/z=285 [M+H]+.

Workup

  1. custompartitioned between saturated aqueous NaHCO3 solution and ethyl acetate
  2. extractionThe aqueous phase is extracted with ethyl acetate
  3. dry with materialthe combined organic phases are dried (MgSO4)
  4. customThe solvent is evaporated
  5. customthe residue is chromatographed on silica gel (cyclohexane/ethyl acetate 100:0→70:30)

Sources & evidence

ORD record
ord-7d867147ffd541b38140cb598cd36b86
Source dataset
uspto-grants-2014_02
Patent number
US08642585B2

Reaction notes

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