2-Nitroethanol → 8-Bromo-3-nitrochroman

HRID 1464698

반응식

HRID 1464698 반응식
[Br:1][C:2]1[CH:9]=[CH:8][CH:7]=[C:4]([CH:5]=O)[C:3]=1[OH:10].[Cl-].C([NH2+]CCCC)CCC.[N+:21]([CH2:24][CH2:25]O)([O-:23])=[O:22].C([BH3-])#N>C(OC(=O)C)CC(C)C.CO.O>[Br:1][C:2]1[CH:9]=[CH:8][CH:7]=[C:4]2[C:3]=1[O:10][CH2:25][CH:24]([N+:21]([O-:23])=[O:22])[CH2:5]2

참가 물질

8

반응물 4

HCID 122522-NitroethanolHCID 498716Cyano-borohydrideHCID 517667N-butylbutan-1-amine hydrochlorideHCID 109105553-Bromo-2-hydroxybenzaldehyde

생성물 1

HCID 190871628-Bromo-3-nitrochroman수율 63%

시약·촉매·용매 3

HCID 887Methanol용매HCID 962Water용매HCID 31276Isoamyl Acetate용매

실험 절차

Commercially available 3-bromosalicylaldehyde (0.5 g; 2.5 mmol), di-n-butylammonium chloride (0.2 g; 1.2 mmol) and 2-nitroethanol (0.36 g; 4.0 mmol) were refluxed for 8 hours in i-pentylacetate with a Dean-Stark apparatus under nitrogen atmosphere. The solvent was evaporated and the product was dissolved in dichloromethane (15 ml) and cyanoborohydride (0.5 g; 8.1 mmol) in methanol (15 ml) was added. The mixture was stirred for 30 minutes at room temperature. Water was added and the mixture extracted with dichloromethane. The phase were separated and the organic layer was dried (MgSO4). The solvent was evaporated yielding 400 mg (63%) of 8-bromo-3-nitrochroman as an oil.

후처리

  1. customThe solvent was evaporated
  2. dissolutionthe product was dissolved in dichloromethane (15 ml)
  3. extractionthe mixture extracted with dichloromethane
  4. customThe phase were separated
  5. dry with materialthe organic layer was dried (MgSO4)
  6. customThe solvent was evaporated

출처 및 근거

ORD 기록
ord-9b0f3df3890e45cca073dab5c798eac6
출처 데이터셋
uspto-grants-1994_04
특허 번호
US05306830

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