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

HRID 966948

Reaction equation

HRID 966948 reaction equation
[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]

Participants

6

Reactant 4

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

Product 1

HCID 136226402-Bromo-6-(1,3-dioxoisoindolin-2-yl)hexanoic AcidYield 91.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-4994cd6bab324fcc93d3c5d25da9512c
Source dataset
uspto-grants-2005_10
Patent number
US06953788B1

Linked notes

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