Bromochloromethane → 2-Bromo-4-methoxy-8,9-dihydro-5,7-dioxabenzocycloheptene

HRID 1161491

反応式

HRID 1161491 の反応式
[Br:1][C:2]1[CH:7]=[C:6]([O:8][CH3:9])[C:5]([OH:10])=[C:4]([CH2:11][CH2:12][OH:13])[CH:3]=1.[CH3:14][Si]([N-][Si](C)(C)C)(C)C.[Na+].BrCCl.[Cl-].[NH4+]>CN(C=O)C.C(OCC)(=O)C>[Br:1][C:2]1[CH:7]=[C:6]([O:8][CH3:9])[C:5]2[O:10][CH2:14][O:13][CH2:12][CH2:11][C:4]=2[CH:3]=1

参加物

7

反応物 4

HCID 6333BromochloromethaneHCID 25517Ammonium ChlorideHCID 2724254Sodium bis(trimethylsilyl)amideHCID 670974744-Bromo-2-(2-hydroxyethyl)-6-methoxyphenol

生成物 1

HCID 595172132-Bromo-4-methoxy-8,9-dihydro-5,7-dioxabenzocycloheptene収率 44.6%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

実験手順

To a solution of 898 mg of 4-bromo-2-(2-hydroxyethyl)-6-methoxyphenol in 10 ml of DMF there was added 1 g of sodium bistrimethylsilylamide while cooling on ice, and the mixture was stirred at room temperature for 30 minutes. After adding 1 ml of bromochloromethane to the reaction mixture, it was stirred at 80° C. for 20 hours under a nitrogen atmosphere. Saturated aqueous ammonium chloride was added to the reaction mixture, and extraction was performed with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate. The desiccating agent was filtered off and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate-heptane) to give the title compound (420 mg) as an oil.

後処理

  1. temperaturewhile cooling on ice
  2. stirringwas stirred at 80° C. for 20 hours under a nitrogen atmosphere
  3. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  4. filtrationThe desiccating agent was filtered off
  5. concentrationthe filtrate was concentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (ethyl acetate-heptane)

出典と根拠

ORDレコード
ord-9fcb4ee3f48e46589890d7e06171e541
出典データセット
uspto-grants-2010_10
特許番号
US07816522B2

関連ノート

読み込み中…