Water → 7-Chloro-1,3-dioxaindane-5-carbaldehyde

HRID 39140

反応式

HRID 39140 の反応式
[Cl:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([OH:11])[C:9]=1[OH:10])[CH:5]=[O:6].[C:12]([O-])([O-])=O.[Cs+].[Cs+].O>CN(C=O)C>[Cl:1][C:2]1[C:9]2[O:10][CH2:12][O:11][C:8]=2[CH:7]=[C:4]([CH:5]=[O:6])[CH:3]=1

参加物

5

反応物 3

HCID 962WaterHCID 10796Cesium carbonateHCID 24681823-Chloro-4,5-dihydroxybenzaldehyde

生成物 1

HCID 6764927-Chloro-1,3-dioxaindane-5-carbaldehyde収率 70.7%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
60 °C

実験手順

To a solution of 3-chloro-4,5-dihydroxybenzaldehyde (8.0 g, 46 mmol) and BrClCH2 (23.9 g, 185 mmol) in dry DMF (100 mL) was added Cs2CO3 (25 g, 190 mmol). The mixture was stirred at 60° C. overnight and was then poured into water. The resulting mixture was extracted with EtOAc (50 mL×3). The combined extracts were washed with brine (100 mL), dried over Na2SO4 and concentrated under reduced pressure to afford 7-chlorobenzo[d][1,3]dioxole-5-carbaldehyde (6.0 g, 70%). 1H NMR (400 MHz, CDCl3) δ 9.74 (s, 1H), 7.42 (d, J=0.4 Hz, 1H), 7.26 (d, J=3.6 Hz, 1H), 6.15 (s, 2H)

後処理

  1. extractionThe resulting mixture was extracted with EtOAc (50 mL×3)
  2. washThe combined extracts were washed with brine (100 mL)
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-965f5a1b080e40169a4f6ccdc792a612
出典データセット
uspto-grants-2013_09
特許番号
US08524767B2

関連ノート

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