1-Bromo-2-Chloroethane → Methyl 1-(4-t-butylphenyl)cyclopropanecarboxylate

HRID 1167209Notes

Reaction equation

HRID 1167209 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([CH2:11][C:12]([O:14][CH3:15])=[O:13])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].C[Si]([N-][Si](C)(C)C)(C)C.[Li+].Br[CH2:27][CH2:28]Cl>C1COCC1>[C:1]([C:5]1[CH:6]=[CH:7][C:8]([C:11]2([C:12]([O:14][CH3:15])=[O:13])[CH2:28][CH2:27]2)=[CH:9][CH:10]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 78491-Bromo-2-ChloroethaneHCID 605629Methyl p-tert-butylphenylacetateHCID 2733832Lithium Hexamethyldisilazide

Product 1

HCID 21893525Methyl 1-(4-t-butylphenyl)cyclopropanecarboxylateYield 93.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

4 g (19.4 mmol) of Methyl 4-tert-butylphenylacetate, 39 mL (1.0 m, 2 Eq.) of lithium bis(trimethylsilyl)amide, and 3 g (2 Eq.) of 1-bromo-2-chloroethane in 100 mL dry THF were reacted as described in Preparation 11, except that the reaction mixture was stirred for one hour at ambient temperature before work-up. This reaction yielded 4.21 g of a brown oil. This material was purified via silica gel chromatography eluting with a gradient solvent of hexanes to hexanes/EtOAc 19:1 to yield the title compound 1.57 g (35%) as a pale yellow solid m.p. 58°-60° C. Calculated for C15H20O2: Theory: C, 77.37; H, 8.81 Found: C, 77.54; H, 8.68.

Workup

  1. customas described in Preparation 11, except that the reaction mixture

Sources & evidence

ORD record
ord-449aa79af9ae45dcb1c6bbcaabea4332
Source dataset
uspto-grants-2003_09
Patent number
US06617351B1

Reaction notes

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