1-Bromo-2-Chloroethane → HCID 4493084, compound

HRID 1631384Notes

Reaction equation

HRID 1631384 reaction equation
[OH:1][N:2]1[C:10](=[O:11])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]1=[O:12].Br[CH2:14][CH2:15][Cl:16].C(N(CC)CC)C>CN(C=O)C>[Cl:16][CH2:15][CH2:14][O:1][N:2]1[C:10](=[O:11])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]1=[O:12]

Participants

5

Reactant 3

HCID 78491-Bromo-2-ChloroethaneHCID 8471TriethylamineHCID 10665N-Hydroxyphthalimide

Product 1

HCID 4493084HCID 4493084, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A 1 L round-bottomed flask was charged 2-hydroxyisoindoline-1,3-dione (16.6 g, 98.71 mmol), followed by DMF (100 mL), then 1-bromo-2-chloroethane (25.2 mL, 296.1 mmol), and then triethylamine (42.1 mL, 296.1 mmol). After stirring at ambient temperature overnight, the reaction mixture was filtered (GF/F) and rinsed with DMF. The filtrate (250 mL) was poured into ice-water (2 L) while stirring, and the resulting precipitate was filtered, rinsed with water, and dried, yielding the crude product as a white solid (21 g). The crude product was triturated with heptane (3×400 mL), filtered and air-dried, giving the product as white solid (17.6 g, 79%).

Workup

  1. filtrationthe reaction mixture was filtered (GF/F)
  2. washrinsed with DMF
  3. additionThe filtrate (250 mL) was poured into ice-water (2 L)
  4. stirringwhile stirring
  5. filtrationthe resulting precipitate was filtered
  6. washrinsed with water
  7. customdried
  8. customyielding the crude product as a white solid (21 g)
  9. customThe crude product was triturated with heptane (3×400 mL)
  10. filtrationfiltered
  11. customair-dried

Sources & evidence

ORD record
ord-8fefd86f8c0b4693ac4c49afc8c82ea2
Source dataset
uspto-grants-2014_07
Patent number
US08791123B2

Reaction notes

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