1,2-Dibromoethane → 8-Nitro-2,3-dihydro-1,4-benzodioxine-6-carbaldehyde

HRID 2178058노트

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HRID 2178058 반응식
O.O.[F-].[K+].[OH:5][C:6]1[CH:7]=[C:8]([CH:11]=[C:12]([N+:15]([O-:17])=[O:16])[C:13]=1[OH:14])[CH:9]=[O:10].Br[CH2:19][CH2:20]Br>CN(C)C=O>[N+:15]([C:12]1[C:13]2[O:14][CH2:19][CH2:20][O:5][C:6]=2[CH:7]=[C:8]([CH:9]=[O:10])[CH:11]=1)([O-:17])=[O:16]

참가 물질

5

반응물 3

HCID 78391,2-DibromoethaneHCID 57489573,4-Dihydroxy-5-nitrobenzaldehydeHCID 23708904Potassium fluoride dihydrate

생성물 1

HCID 218738188-Nitro-2,3-dihydro-1,4-benzodioxine-6-carbaldehyde수율 62.1%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
130 °C

실험 절차

To a mixture of potassium fluoride dihydrate (2.573 g, 27.3 mmol), and 3,4-dihydroxy-5-nitrobenzaldehyde (500 mg, 2.73 mmol) in N,N-dimethylformamide (20 mL) was added 1,2-dibromoethane (3.8 mL, 43.7 mmol), and the mixture was heated at 130° C. for 17 h. The reaction mixture was quenched with water followed by a standard aqueous/EtOAc workup and purified by column chromatography on silica gel (petroleum ether/ethyl acetate=15:1) to give Intermediate 45 (350 mg, yield 62.1%).

후처리

  1. customThe reaction mixture was quenched with water
  2. custompurified by column chromatography on silica gel (petroleum ether/ethyl acetate=15:1)

출처 및 근거

ORD 기록
ord-65a962644cbc41dfbd7d7e70804f1061
출처 데이터셋
uspto-grants-2015_06
특허 번호
US09067893B2

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