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

HRID 1019101

Reaction equation

HRID 1019101 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.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]

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 91.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

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 bromine (12.7 mL, 246 mmol) dropwise. 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 to 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).

Workup

  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. customto give a solid
  6. customCollect the solid
  7. filtrationby filtration
  8. customdry

Sources & evidence

ORD record
ord-1c23e492c8e14c2386e23871275d968f
Source dataset
uspto-grants-2002_11
Patent number
US06486193B2

Linked notes

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