Diiodomethane → HCID 18434231, compound

HRID 2306472Notes

Reaction equation

HRID 2306472 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:10]2[CH:20]=[CH:19][C:13]([O:14][Si](C)(C)C)=[CH:12][CH:11]=2)=[CH2:9])=[CH:4][CH:3]=1.Br[C:22]1C=CC(C(C2C=CC(O)=CC=2)=C)=CC=1.C[Si](C)(C)N[Si](C)(C)C.C(I)I>CCOCC.[Zn].Cl[Cu]>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([C:10]3[CH:20]=[CH:19][C:13]([OH:14])=[CH:12][CH:11]=3)[CH2:22][CH2:9]2)=[CH:4][CH:3]=1

Participants

8

Reactant 4

HCID 6346DiiodomethaneHCID 13838HexamethyldisilazaneHCID 18434141HCID 18434141, compoundHCID 18434314HCID 18434314, compound

Product 1

HCID 18434231HCID 18434231, compound

Reagents, catalysts & solvents 3

HCID 23994ZincCatalystHCID 62652Cuprous chlorideCatalystHCID 3283Diethyl EtherSolvent3×

Procedure

Eg) A mixture of 457 mg of zinc dust and 692 mg of CuCl in 15 ml of ether is heated under reflux under argon. Subsequently, a solution of 934 mg of [4-[1-(4-bromo-phenyl)-vinyl]-phenoxy]-trimethyl-silane in 15 ml of ether, prepared from 748 mg of 4-[1-(4-bromo-phenyl)-vinyl]-phenol (Ex. Ef) and 14 ml of hexamethyldisilazane under reflux, is added dropwise and thereafter 0.56 ml of methylene iodide is added. The reaction mixture is heated under reflux and diluted with ether. The residue is washed with ether and the filtrate is washed with water, dried and concentrated. The crude product is purified over silica gel with ethyl acetate-hexane as the eluent. 4-(1-(4-Bromo-phenyl)-cyclopropyl)-phenol is obtained as a brown oil, MS: m/e 288 (M+H+, 1Br).

Workup

  1. temperatureis heated
  2. temperatureunder reflux under argon
  3. temperatureunder reflux
  4. additionis added dropwise
  5. temperatureThe reaction mixture is heated
  6. temperatureunder reflux
  7. washThe residue is washed with ether
  8. washthe filtrate is washed with water
  9. customdried
  10. concentrationconcentrated
  11. customThe crude product is purified over silica gel with ethyl acetate-hexane as the eluent

Sources & evidence

ORD record
ord-49f230f1ce2d47a59cd2b165cfb6b7df
Source dataset
uspto-grants-2002_08
Patent number
US06441177B1

Reaction notes

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