Sulfuric Acid → Tert-butyl 1-(4-bromophenyl)cyclopropanecarboxylate

HRID 969148Notes

Reaction equation

HRID 969148 reaction equation
[CH3:1][C:2](=[CH2:4])[CH3:3].[Br:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]2([C:15]([OH:17])=[O:16])[CH2:14][CH2:13]2)=[CH:8][CH:7]=1.S(=O)(=O)(O)O>>[Br:5][C:6]1[CH:7]=[CH:8][C:9]([C:12]2([C:15]([O:17][C:2]([CH3:4])([CH3:3])[CH3:1])=[O:16])[CH2:14][CH2:13]2)=[CH:10][CH:11]=1

Participants

4

Reactant 3

HCID 1118Sulfuric AcidHCID 8255IsobutyleneHCID 162279661-(4-Bromophenyl)cyclopropane-1-carboxylic acid

Product 1

HCID 66661920Tert-butyl 1-(4-bromophenyl)cyclopropanecarboxylate

Procedure

Isobutylene (80.0 mL, 0.847 mol) was passed through a mixture of 1-(4-bromophenyl)cyclopropanecarboxylic acid (10.0 g, 0.0415 mol, example 238, step 1) and sulfuric acid (1.0 mL, 0.019 mol) at −78° C. The mixture was sealed and was stirred at room temperature overnight. The isobutylene was evaporated at room temperature and the residue was dissolved in ethyl acetate (100 mL), and washed with water and brine successively. The organic layer was dried over Na2SO4, filtered, and concentrated under reduced pressure to give the desired product.

Workup

  1. customThe mixture was sealed
  2. customThe isobutylene was evaporated at room temperature
  3. dissolutionthe residue was dissolved in ethyl acetate (100 mL)
  4. washwashed with water and brine successively
  5. dry with materialThe organic layer was dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-f90aa1da827a42ce8c58896e8d2de47d
Source dataset
uspto-grants-2007_12
Patent number
US07304081B2

Reaction notes

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