Water → 2-(bromomethyl)-5-fluoro-7-(methylsulfonyl)-4H-1,3-benzodioxine

HRID 452468노트

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HRID 452468 반응식
[F:1][C:2]1[C:3]([CH2:13][OH:14])=[C:4]([OH:12])[CH:5]=[C:6]([S:8]([CH3:11])(=[O:10])=[O:9])[CH:7]=1.[Br:15][CH2:16][CH:17](OC)OC.OS(O)(=O)=O.O>C1COCC1>[Br:15][CH2:16][CH:17]1[O:12][C:4]2[CH:5]=[C:6]([S:8]([CH3:11])(=[O:10])=[O:9])[CH:7]=[C:2]([F:1])[C:3]=2[CH2:13][O:14]1

참가 물질

6

반응물 4

HCID 962WaterHCID 1118Sulfuric AcidHCID 816722-Bromo-1,1-dimethoxyethaneHCID 668875163-Fluoro-2-(hydroxymethyl)-5-(methylsulfonyl)phenol

생성물 1

HCID 668876212-(bromomethyl)-5-fluoro-7-(methylsulfonyl)-4H-1,3-benzodioxine수율 43.2%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

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온도
60 °C

실험 절차

3-fluoro-2-(hydroxymethyl)-5-(methylsulfonyl)phenol (0.11 g, 0.52 mmol) was dissolved in THF (dry) (5 ml). 2-bromo-1,1-dimethoxyethane (0.63 ml, 5.2 mmol) was added followed by concentrated H2SO4 (1 ml). The mixture was heated at 60° C. for 1 h. Water was added and the mixture extracted with EtOAc twice. The combined extracts were washed with brine and concentrated. Purification by flash column chromatography (isooctane/EtOAc) gave the title compound (0.073 g). MS m/z (rel. intensity, 70 eV) 326 (M+, 8), 324 (M+, 8), 231 (17), 202 (bp), 139 (21), 95 (42), 75 (34).

후처리

  1. extractionthe mixture extracted with EtOAc twice
  2. washThe combined extracts were washed with brine
  3. concentrationconcentrated
  4. customPurification by flash column chromatography (isooctane/EtOAc)

출처 및 근거

ORD 기록
ord-919018b17fff4f24a466ce087ab54cd3
출처 데이터셋
uspto-grants-2013_07
특허 번호
US08492372B2

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