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

HRID 452468ノート

反応式

HRID 452468 の反応式
[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

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
60 °C

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-919018b17fff4f24a466ce087ab54cd3
出典データセット
uspto-grants-2013_07
特許番号
US08492372B2

反応ノート

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