1-Bromo-2-Chloroethane → HCID 18184158, compound

HRID 1358630Notes

Reaction equation

HRID 1358630 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])(C)C.Br[CH2:17][CH2:18]Cl.[CH2:20]1COC[CH2:21]1>C[Si]([N-][Si](C)(C)C)(C)C.[Li+]>[CH2:1]([C:5]1[CH:6]=[CH:7][C:8]([C:11]2([C:12]([O:14][CH3:15])=[O:13])[CH2:18][CH2:17]2)=[CH:9][CH:10]=1)[CH2:4][CH2:20][CH3:21]

Participants

5

Reactant 3

HCID 78491-Bromo-2-ChloroethaneHCID 8028TetrahydrofuranHCID 605629Methyl p-tert-butylphenylacetate

Product 1

HCID 18184158HCID 18184158, compound

Reagents, catalysts & solvents 1

HCID 2733832Lithium HexamethyldisilazideCatalyst

Procedure

4 g (19.4 mmol) of Methyl 4-tert-butylphenylacetate, 39 mg (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 hexane to hexane/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-37dc8cc7167a449db7fd0596de3f1f85
Source dataset
uspto-grants-2003_07
Patent number
US06596716B2

Reaction notes

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