Dimethyl Sulfate → 4-Bromo-2-chloro-6-methylanisole

HRID 1110875노트

반응식

HRID 1110875 반응식
[Br:1][C:2]1[CH:7]=[C:6]([CH3:8])[C:5]([OH:9])=[C:4]([Cl:10])[CH:3]=1.[C:11]([O-])([O-])=O.[K+].[K+].S(OC)(OC)(=O)=O>CC(C)=O>[Br:1][C:2]1[CH:7]=[C:6]([CH3:8])[C:5]([O:9][CH3:11])=[C:4]([Cl:10])[CH:3]=1

참가 물질

5

반응물 3

HCID 6497Dimethyl SulfateHCID 11430Potassium CarbonateHCID 820314-Bromo-6-chloro-o-cresol

생성물 1

HCID 30218344-Bromo-2-chloro-6-methylanisole

시약·촉매·용매 1

HCID 180Acetone용매

실험 절차

4-Bromo-2-chloro-6-methylphenol (50 g, 0.225 mole) and K2CO3 (31.8 g, 0.23 mole) were combined in acetone (300 ml). Dimethyl sulfate (32 ml, 0.34 mole) was added dropwise and the mixture stirred 22 hours at room temperature, filtered and concentrated to an oil in vacuo. The oil was taken up in 250 ml ether, washed 2×2N NaOH, 1×saturated NaHCO3, 2×brine, dried over MgSO4, reconcentrated to an oil and distilled to yield purified title product, 42.9 g, b.p. 122°-124°0.9 mm, pnmr/CDCl3 /delta/TMS: 2.3 (s, 3H), 3.8 (s, 3H), 7.3 (q, 2H).

후처리

  1. filtrationfiltered
  2. concentrationconcentrated to an oil in vacuo
  3. washwashed 2×2N NaOH, 1×saturated NaHCO3, 2×brine
  4. dry with materialdried over MgSO4
  5. distillationdistilled
  6. customto yield
  7. custompurified title product, 42.9 g, b.p. 122°-124°0.9 mm

출처 및 근거

ORD 기록
ord-8e93d94968414fc6b7db7d8b031b10a1
출처 데이터셋
uspto-grants-1990_12
특허 번호
US04977178

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