Dimethyl Sulfate → 1-Chloro-3-fluoro-2-(methoxymethyl)benzene

HRID 2256974Notes

Reaction equation

HRID 2256974 reaction equation
[Cl:1][C:2]1[CH:9]=[CH:8][CH:7]=[C:6]([F:10])[C:3]=1[CH2:4][OH:5].[OH-].[Na+].S(OC)(O[CH3:17])(=O)=O>ClCCl.O.S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC>[Cl:1][C:2]1[CH:9]=[CH:8][CH:7]=[C:6]([F:10])[C:3]=1[CH2:4][O:5][CH3:17]

Participants

7

Reactant 3

HCID 6497Dimethyl SulfateHCID 14798Sodium HydroxideHCID 918682-Chloro-6-fluorobenzyl alcohol

Product 1

HCID 537737161-Chloro-3-fluoro-2-(methoxymethyl)benzeneYield 50.2%

Reagents, catalysts & solvents 3

HCID 94433Tetrabutylammonium hydrogen sulfateCatalystHCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

2-Chloro-6-fluorobenzyl alcohol (50 g) was stirred in dichloromethane and a solution of sodium hydroxide (32 g) in water was added. After 30 minutes stirring the mixture was cooled to 0° C. when dimethyl sulphate (47 g) and tetrabutyl-ammonium hydrogen-sulphate (1 g) were added dropwise. The mixture was allowed to warm to room temperature and stirred for 3 hours. It was quenched with water and extracted with dichloromethane. The organic extract was washed with water, dried (anhydrous magnesium sulphate) and filtered. The filtrate was evaporated to dryness and the residue distilled under reduced pressure yielding 1-chloro-3-fluoro-2-methoxymethylbenzene (27.3 g) b.p. 82°-95° C./24mm Hg.

Workup

  1. additionwere added dropwise
  2. stirringstirred for 3 hours
  3. customIt was quenched with water
  4. extractionextracted with dichloromethane
  5. extractionThe organic extract
  6. washwas washed with water
  7. dry with materialdried (anhydrous magnesium sulphate)
  8. filtrationfiltered
  9. customThe filtrate was evaporated to dryness
  10. distillationthe residue distilled under reduced pressure

Sources & evidence

ORD record
ord-536655d9bbd74f29a2744391a9b685f0
Source dataset
uspto-grants-1997_08
Patent number
US05656573

Reaction notes

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