Water → 7-Amino-4-bromo-2,3-dihydro-2,2-dimethylbenzofuran

HRID 52654

反応式

HRID 52654 の反応式
[NH2:1][C:2]1[C:10]2[O:9][C:8]([CH3:12])([CH3:11])[CH2:7][C:6]=2[CH:5]=[CH:4][CH:3]=1.[Br:13]N1C(=O)CCC1=O.O>CN(C)C=O>[NH2:1][C:2]1[C:10]2[O:9][C:8]([CH3:12])([CH3:11])[CH2:7][C:6]=2[C:5]([Br:13])=[CH:4][CH:3]=1

参加物

5

反応物 3

HCID 962WaterHCID 67184N-bromobutanimideHCID 916972,2-Dimethyl-2,3-dihydro-1-benzofuran-7-amine

生成物 1

HCID 537220087-Amino-4-bromo-2,3-dihydro-2,2-dimethylbenzofuran収率 83.3%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒2 回

実験手順

A stirred solution of 10.0 grams (0.061 mole) of 7-amino-2,3-dihydro-2,2-dimethylbenzofuran in 150 mL of N,N-dimethylformamide was cooled in an ice-water bath, and a solution of 10.9 grams (0.061 mole) of N-bromosuccinimide in 50 mL of N,N-dimethylformamide was added in one portion. Upon completion of addition, the reaction mixture was maintained in the ice-water bath for about one hour. After this time the reaction mixture was poured into about 600 mL of water. The mixture was then extracted with two 200 mL portions of diethyl ether. The combined extracts were washed with two 100 mL portions of an aqueous 10% lithium chloride solution. The organic layer was dried with magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure, yielding 12.3 grams of 7-amino-4-bromo-2,3-dihydro-2,2-dimethylbenzofuran. The NMR spectrum was consistent with the proposed structure.

後処理

  1. additionUpon completion of addition
  2. extractionThe mixture was then extracted with two 200 mL portions of diethyl ether
  3. washThe combined extracts were washed with two 100 mL portions of an aqueous 10% lithium chloride solution
  4. dry with materialThe organic layer was dried with magnesium sulfate
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated under reduced pressure

出典と根拠

ORDレコード
ord-2858beaef18e4b99a94fa34a60c10f7c
出典データセット
uspto-grants-1997_04
特許番号
US05616718

関連ノート

読み込み中…