Bromine → 2-Bromo-6-(1,3-dioxoisoindolin-2-yl)hexanoic Acid

HRID 1835663

反応式

HRID 1835663 の反応式
[C:1]1(=[O:19])[N:5]([CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][C:11]([OH:13])=[O:12])[C:4](=[O:14])[C:3]2=[CH:15][CH:16]=[CH:17][CH:18]=[C:2]12.[Br:20]Br.S(=O)(O)[O-].[Na+].C(=O)(O)[O-].[Na+]>O>[Br:20][CH:10]([CH2:9][CH2:8][CH2:7][CH2:6][N:5]1[C:4](=[O:14])[C:3]2=[CH:15][CH:16]=[CH:17][CH:18]=[C:2]2[C:1]1=[O:19])[C:11]([OH:13])=[O:12]

参加物

6

反応物 4

HCID 24408BromineHCID 781851,3-Dihydro-1,3-dioxo-2H-isoindole-2-hexanoic acidHCID 516892Sodium BicarbonateHCID 23665763Sodium Bisulfite

生成物 1

HCID 136226402-Bromo-6-(1,3-dioxoisoindolin-2-yl)hexanoic Acid収率 91.5%

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

Combine 6-phthalimidohexanoic acid (12.7 g, 48 mmol) and dry red phosphorous (1.95 g, 63 mmol). Cool in an ice bath and add dropwise bromine (12.7 mL, 246 mmol). Warm to room temperature and then heat to 80° C. After 3 hours, cool the reaction mixture to ambient temperature, pour into water (300 mL) containing sodium bisulfite, and neutralize using solid sodium bicarbonate and extract with diethyl ether (about 150 mL). Acidify the aqueous layer with concentrated hydrochloric acid give a solid. Collect the solid by filtration and dry to give the title compound (15 g, 91.5% yield, 73.2% for both steps).

後処理

  1. temperatureCool in an ice bath
  2. temperatureheat to 80° C
  3. temperaturecool the reaction mixture to ambient temperature
  4. extractionextract with diethyl ether (about 150 mL)
  5. customgive a solid
  6. customCollect the solid
  7. filtrationby filtration
  8. customdry

出典と根拠

ORDレコード
ord-f541110b74344d0c8c7ddcb904b56ded
出典データセット
uspto-grants-2004_08
特許番号
US06770640B1

関連ノート

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