Aminoacetaldehyde dimethyl acetal → 5-Bromo-2-fluorobenzylidene-2,2-dimethoxyethylamine

HRID 272777ノート

反応式

HRID 272777 の反応式
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([F:10])=[C:6]([CH:9]=1)[CH:7]=O.[CH3:11][O:12][CH:13]([O:16][CH3:17])[CH2:14][NH2:15]>C1(C)C=CC=CC=1>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([F:10])=[C:6]([CH:9]=1)[CH:7]=[N:15][CH2:14][CH:13]([O:16][CH3:17])[O:12][CH3:11]

参加物

4

反応物 2

HCID 89728Aminoacetaldehyde dimethyl acetalHCID 7363275-Bromo-2-fluorobenzaldehyde

生成物 1

HCID 692158965-Bromo-2-fluorobenzylidene-2,2-dimethoxyethylamine

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

実験手順

A mixture of 5-bromo-2-fluorobenzaldehyde (15 g, 74 mmol) and 2,2-dimethoxy-ethylamine (7.77 g, 74 mmol) in toluene (142 mL) was heated to reflux for 30 minutes using a Dean-Stark trap to remove water. The solution was then concentrated under vacuum to provide 5-bromo-2-fluorobenzylidene-2,2-dimethoxyethylamine. 5-Bromo-2-fluorobenzylidene-2,2-dimethoxyethylamine and cold concentrated sulfuric acid (28 mL) were added separately, dropwise, over a period of 20 minutes to concentrated sulfuric acid (83 mL) at 140° C. The mixture was stirred at 135° C. for 30 minutes, allowed to cool, and carefully poured onto ice. Filtered to remove solids and the mixture was washed with dichloromethane. The aqueous layer was made basic by cautious addition of 50% sodium hydroxide solution, and extracted with diethyl ether. Combined ether layers were dried (MgSO4), filtered and concentrated under vacuum to provide 310 mg (2%) of the desired product. MS (ESI) m/e 226 (M+H)+.

後処理

  1. temperaturewas heated
  2. temperatureto reflux for 30 minutes
  3. customto remove water
  4. concentrationThe solution was then concentrated under vacuum

出典と根拠

ORDレコード
ord-ea9e706d576e4638bc718a6c87ecf8c6
出典データセット
uspto-grants-2008_11
特許番号
US07456169B2

反応ノート

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