2-Nitroethanol → 8-Bromo-3-nitrochroman

HRID 1464698ノート

反応式

HRID 1464698 の反応式
[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

参加物

8

反応物 4

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

生成物 1

HCID 190871628-Bromo-3-nitrochroman収率 63%

試薬・触媒・溶媒 3

HCID 887Methanol溶媒HCID 962Water溶媒HCID 31276Isoamyl Acetate溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-9b0f3df3890e45cca073dab5c798eac6
出典データセット
uspto-grants-1994_04
特許番号
US05306830

反応ノート

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