Allyl bromide → HCID 68468944, compound

HRID 2235227Notes

Reaction equation

HRID 2235227 reaction equation
[CH2:1]1[CH2:5]OC[CH2:2]1.[CH2:6]([O:8][C:9](=[O:22])[CH2:10][C:11]([C:14]1[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][C:15]=1[Cl:21])([CH3:13])[CH3:12])[CH3:7].[Li+].CC([N-]C(C)C)C.C(Br)C=C>C(OCC)C>[CH2:6]([O:8][C:9](=[O:22])[CH:10]([C:11]([C:14]1[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][C:15]=1[Cl:21])([CH3:13])[CH3:12])[CH2:5][CH:1]=[CH2:2])[CH3:7]

Participants

6

Reactant 4

HCID 7841Allyl bromideHCID 8028TetrahydrofuranHCID 2724682Lithium diisopropylamideHCID 68466821HCID 68466821, compound

Product 1

HCID 68468944HCID 68468944, compoundYield 52%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Cool a THF solution of 1.0 equivalent of 3-(2,4-Dichloro-phenyl)-3-methyl-butyric acid ethyl ester, obtained above, to −78° C., treat with LDA (2.0 eq), followed by allyl bromide (1.1 eq), warm to room temperature and stir 17 h. Quench reaction with NH4Cl, dilute with diethyl ether, wash organics with 0.1 N HCl, brine, dry over sodium sulfate, filter and evaporate. Chromatography, (silica, hexanes/EtOAc, 98:2) provides 2-[1-(2,4-dichloro-phenyl)-1-methyl-ethyl]-pent-4-enoic acid ethyl ester in 52% yield.

Workup

  1. customobtained above, to −78° C.
  2. customQuench
  3. customreaction with NH4Cl
  4. washwash organics with 0.1 N HCl, brine
  5. dry with materialdry over sodium sulfate
  6. filtrationfilter
  7. customevaporate

Sources & evidence

ORD record
ord-0429f6ccacfa40c1b492769ad28070af
Source dataset
uspto-grants-2010_05
Patent number
US07713979B2

Reaction notes

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