1,3-Dibromopropane → HCID 67099665, compound

HRID 2078287Notes

Reaction equation

HRID 2078287 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10])=[C:4]([I:14])[CH:3]=1.[H-].[Na+].Br[CH2:18][CH2:19][CH2:20]Br>CN(C=O)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([C:9]([O:11][CH2:12][CH3:13])=[O:10])[CH2:20][CH2:19][CH2:18]2)=[C:4]([I:14])[CH:3]=1

Participants

5

Reactant 3

HCID 80011,3-DibromopropaneHCID 24758Sodium hydride2×HCID 67099944HCID 67099944, compound

Product 1

HCID 67099665HCID 67099665, compoundYield 45.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Ethyl 2-(4-chloro-2-iodophenyl)acetate (3.95 g, 12 mmol) was mixed in DMF (80 mL) in a round bottom flask. NaH (60% dispersion in mineral oil (0.54 g, 13 mmol)) was added, and the reaction mixture was stirred for 15 minutes under a nitrogen atmosphere. 1,3-dibromopropane (1.4 mL, 13 mmol, 1.1 eq) was added via syringe, and the reaction mixture was stirred for 2 hours. An additional 1.10 eq NaH (60% dispersion in mineral oil (0.54 g, 13 mmol)) was added, and the reaction was stirred for 3 hours. The reaction mixture was quenched with water and diluted with EtOAc. The organic layer was separated, washed with water and brine, dried (MgSO4), and concentrated in vacuo to give an orange oil. The crude product was purified by silica flash chromatography (0-30% DCM/hexane) to give the desired compound as a light yellow oil (2.01 g). MS (m/e)=365.1 (M+H)+.

Workup

  1. stirringthe reaction mixture was stirred for 2 hours
  2. stirringthe reaction was stirred for 3 hours
  3. customThe reaction mixture was quenched with water
  4. additiondiluted with EtOAc
  5. customThe organic layer was separated
  6. washwashed with water and brine
  7. dry with materialdried (MgSO4)
  8. concentrationconcentrated in vacuo
  9. customto give an orange oil
  10. customThe crude product was purified by silica flash chromatography (0-30% DCM/hexane)

Sources & evidence

ORD record
ord-922dda0f2b444268a83b2c997f17a8e1
Source dataset
uspto-grants-2011_04
Patent number
US07928139B2

Reaction notes

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