Potassium Carbonate → 2-[(2-Chloro-4-fluorophenyl)methyl]-4,4-dimethyl-1,2-oxazolidin-3-one

HRID 231441Notes

Reaction equation

HRID 231441 reaction equation
[CH3:1][C:2]1([CH3:8])[CH2:6][O:5][NH:4][C:3]1=[O:7].[Cl:9][C:10]1[CH:17]=[C:16]([F:18])[CH:15]=[CH:14][C:11]=1[CH2:12]Br.C(=O)([O-])[O-].[K+].[K+]>C(#N)C.O1CCOCCOCCOCCOCCOCC1>[Cl:9][C:10]1[CH:17]=[C:16]([F:18])[CH:15]=[CH:14][C:11]=1[CH2:12][N:4]1[C:3](=[O:7])[C:2]([CH3:8])([CH3:1])[CH2:6][O:5]1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 6421514,4-Dimethyl-1,2-oxazolidin-3-oneHCID 27250621-(Bromomethyl)-2-chloro-4-fluorobenzene

Product 1

HCID 131925732-[(2-Chloro-4-fluorophenyl)methyl]-4,4-dimethyl-1,2-oxazolidin-3-oneYield 107.5%

Reagents, catalysts & solvents 2

HCID 2855718-Crown-6CatalystHCID 6342AcetonitrileSolvent

Procedure

By the method of Example 6, Step B, 95.6 g (0.83 mole) of 4,4-dimethyl-3-isoxazolidinone, 186 g (0.83 mole) of 2-chloro-4-fluorobenzyl bromide, 114.7 g (0.83 mole) of potassium carbonate, and 2.2 g (0.008 mole) of 1,4,7,10,13,16-hexaoxacyclooctadecane were reacted at room temperature in 1500 ml of acetonitrile, yielding 230 g of impure 2-[(2-chloro-4-fluorophenyl)methyl]-4,4-dimethyl-3-isoxazolidinone. The nmr spectrum was consistent with the proposed structure.

Sources & evidence

ORD record
ord-032edfa95986474791a59a65cc58daa4
Source dataset
uspto-grants-1989_07
Patent number
US04846882

Reaction notes

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