Sulfur Dioxide → 4'-Methoxybiphenyl-4-sulfonyl chloride

HRID 352400노트

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HRID 352400 반응식
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([O:14][CH3:15])=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.C([Li])CCC.S(=O)=O.COC1C=CC(C2C=CC(S(O)=O)=CC=2)=CC=1.[Li].[S:42](Cl)([Cl:45])(=[O:44])=[O:43]>O1CCCC1>[CH3:15][O:14][C:11]1[CH:12]=[CH:13][C:8]([C:5]2[CH:6]=[CH:7][C:2]([S:42]([Cl:45])(=[O:44])=[O:43])=[CH:3][CH:4]=2)=[CH:9][CH:10]=1

참가 물질

7

반응물 5

HCID 1119Sulfur Dioxide2회HCID 24648Sulfuryl chlorideHCID 40340054-Bromo-4'-methoxybiphenylHCID 69743094Lithium 4-(4'-methoxyphenyl)phenylsulfinic acidHCID 178418339Butyllithium

생성물 1

HCID 27947504'-Methoxybiphenyl-4-sulfonyl chloride수율 99.7%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

Part B: 5.2 grams (20 mmol) of 4-(4′-bromophenyl)-anisole was dissolved in 100 mL of anhydrous tetrahydrofuran and placed under nitrogen to cool to −78 C. To this flask was added 8.0 mL of 2.5 molar butyl lithium over 10 minutes. In an adjacent flask was added 100 mL of anhydrous tetrahydrofuran which was cooled to −60 C and a stream of sulfur dioxide was added through a dispersion tube while the system is under nitrogen atmosphere. After the addition of approximately 10 mL of liquid sulfur dioxide the dispersion tube was removed and the cold sulfur dioxide solution was transferred by a cannula to the stirred aryl lithium solution over five minutes. After one hour at −70 C the contents were warmed to room temperature and the solution was concentrated to dryness to yield a crude lithium sulfinate. The crude lithium 4-(4′-methoxyphenyl)phenylsulfinic acid was slurried in 100 mL of dry hexanes under nitrogen atmosphere and cooled to 0 C. To this cooled suspension was added 2.45 grams (18.1 mmol) of sulfuryl chloride and the suspension was allowed to warm to room temperature. The contents were concentrated by rotory evaporation to yield 5.1 grams of crude 4-(4′-methoxyphenyl)phenyl-sulfonyl chloride which was purified by recrystallization from chloroform.

후처리

  1. temperatureto cool to −78 C
  2. temperaturewas cooled to −60 C
  3. customwas removed
  4. concentrationthe solution was concentrated to dryness
  5. customto yield a crude lithium sulfinate
  6. temperaturecooled to 0 C
  7. temperatureto warm to room temperature
  8. concentrationThe contents were concentrated by rotory evaporation

출처 및 근거

ORD 기록
ord-8e8171dc5ea04f87aa0adcb831b48eb0
출처 데이터셋
uspto-grants-2004_06
특허 번호
US06747027B1

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