Dimethylformamide → Butyl 1-(4-iodophenyl)cyclopropane-1-carboxylate

HRID 1274262Notes

Reaction equation

HRID 1274262 reaction equation
[I:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([C:11]([OH:13])=O)[CH2:10][CH2:9]2)=[CH:4][CH:3]=1.CN([CH:17]=[O:18])C.[C:19](Cl)(=O)[C:20](Cl)=O.[CH2:25](Cl)Cl>>[I:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2([C:11]([O:18][CH2:17][CH2:25][CH2:19][CH3:20])=[O:13])[CH2:9][CH2:10]2)=[CH:6][CH:7]=1

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 6344DichloromethaneHCID 65578Oxalyl chlorideHCID 217064771-(4-Iodophenyl)cyclopropane-1-carboxylic acid

Product 1

HCID 21706508Butyl 1-(4-iodophenyl)cyclopropane-1-carboxylateYield 62%

Procedure

To a solution of 1-(4-iodophenyl)cyclopropane-1-carboxylic acid (7.98 g, 27 mmol) in methylene chloride (200 mL) containing DMF (0.25 mL) was added dropwise over 30 minutes oxalyl chloride (3.2 mL). The mixture was stirred for 1 hour, and the solvent was removed under reduced pressure. The residue was taken up in THF (100 mL), and potassium t butoxide (1M in THF, 35 mL) was added. After 30 minutes, the mixture was diluted with hexane, washed with water, dried, filtered and evaporated. The solid residue was recrystallized from methanol to give t butyl 1-(4-iodophenyl)cyclopropane-1-carboxylate (5.74 g, 16.6 mmol, 62%).

Workup

  1. customthe solvent was removed under reduced pressure
  2. additionpotassium t butoxide (1M in THF, 35 mL) was added
  3. waitAfter 30 minutes
  4. additionthe mixture was diluted with hexane
  5. washwashed with water
  6. customdried
  7. filtrationfiltered
  8. customevaporated
  9. customThe solid residue was recrystallized from methanol

Sources & evidence

ORD record
ord-126a96272b944977819e6671943880eb
Source dataset
uspto-grants-2000_12
Patent number
US06156784

Reaction notes

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