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

HRID 343031

Reaction equation

HRID 343031 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./24 mm 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-9da017397fee4bc88f32bec3d1902e8c
Source dataset
uspto-grants-1999_01
Patent number
US05859283

Linked notes

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