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

HRID 468274

반응식

HRID 468274 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

HCID 6764927-Chloro-1,3-dioxaindane-5-carbaldehyde수율 70.7%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
60 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-3e69c228eb014dce86571dae808208b0
출처 데이터셋
uspto-grants-2014_01
특허 번호
US08623905B2

연결된 노트

불러오는 중…