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

HRID 966948

反応式

HRID 966948 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.OS([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 91.9%

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

Treat dropwise a mixture of 6-phthalimidocaproic acid (12.7 g, 48 mmol) and dry red phosphorous (1.95 g, 63 mmol) with bromine (12.7 mL, 246 mmol) at 0° C. Warm the resulting lumpy mixture to room temperature and heat to 80° C. for 3 hours. Cool the reaction mixture to room temperature, pour into water (300 mL) containing NaHSO3, and neutralize using solid NaHCO3. Wash the aqueous layer with diethyl ether (150 mL) and acidify with concentrated hydrochloric acid. Collect the pale yellow precipitate by filtration and dry to give 2-bromo-6-phthalimidocaproic acid (15 g, 91.5% yield).

後処理

  1. additionTreat dropwise
  2. temperatureheat to 80° C. for 3 hours
  3. temperatureCool the reaction mixture to room temperature
  4. washWash the aqueous layer with diethyl ether (150 mL)
  5. customCollect the pale yellow precipitate
  6. filtrationby filtration
  7. customdry

出典と根拠

ORDレコード
ord-4994cd6bab324fcc93d3c5d25da9512c
出典データセット
uspto-grants-2005_10
特許番号
US06953788B1

関連ノート

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