Sodium Chloride → 1,3-Dibromo-5-(methylsulfanyl)benzene

HRID 653622노트

반응식

HRID 653622 반응식
C([Li])CCC.[Br:6][C:7]1[CH:12]=[C:11](Br)[CH:10]=[C:9]([Br:14])[CH:8]=1.[CH3:15][S:16]SC.[Cl-].[Na+]>CCOCC.O1CCCC1.C(OCC)(=O)C>[Br:6][C:7]1[CH:12]=[C:11]([S:16][CH3:15])[CH:10]=[C:9]([Br:14])[CH:8]=1

참가 물질

8

반응물 4

HCID 5234Sodium ChlorideHCID 12232Dimethyl DisulfideHCID 122791,3,5-TribromobenzeneHCID 178418339Butyllithium

생성물 1

HCID 190104071,3-Dibromo-5-(methylsulfanyl)benzene

시약·촉매·용매 3

HCID 3283Diethyl Ether용매HCID 8028Tetrahydrofuran용매HCID 8857Ethyl Acetate용매

실험 절차

A 2.5M solution of n-butyllithium (42 mL; 0.105M) was added over 25 mins. to a vigorously stirred suspension of 1,3,5-tribromobenzene (31.5 G; 0.1M) in 1.6 L of anhydrous ether and 400 mL of anhydrous tetrahydrofuran under nitrogen at -78°. After stirring the mixture 30 minutes, 2 equivalents of dimethyldisulfide was added dropwise. The resulting mixture was stirred at R.T. overnight. 150 mL of sat'd sodium chloride solution was cautiously added. 500 mL of ethyl acetate was added. The organic phase was separated, and dried over anhyd. magnesium sulfate. Solvent removal gave a crude product, which was purified on silica gel using hexane as solvent. The desired product was isolated and distilled at 107°-110°/~1 mm to give 18 G of 3,5-dibromothioanisole as a colorless liquid, which slowly solidified on standing.

후처리

  1. additionwas added dropwise
  2. customThe organic phase was separated
  3. customdried over anhyd
  4. customSolvent removal
  5. customgave a crude product, which
  6. customwas purified on silica gel

출처 및 근거

ORD 기록
ord-4124a0cc7c534584a11046d859077aba
출처 데이터셋
uspto-grants-1992_07
특허 번호
US05128335

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