Water → Trimethyl(2,3,2'-trifluoro-4'-iodobiphenyl-4-yl)silane

HRID 1645458Notes

Reaction equation

HRID 1645458 reaction equation
[Li]CCCC.Br[C:7]1[CH:12]=[CH:11][C:10]([C:13]2[CH:18]=[CH:17][C:16]([Si:19]([CH3:22])([CH3:21])[CH3:20])=[C:15]([F:23])[C:14]=2[F:24])=[C:9]([F:25])[CH:8]=1.[I:26]CCI.O>C1COCC1.C(OC)(C)(C)C>[CH3:20][Si:19]([CH3:22])([CH3:21])[C:16]1[CH:17]=[CH:18][C:13]([C:10]2[CH:11]=[CH:12][C:7]([I:26])=[CH:8][C:9]=2[F:25])=[C:14]([F:24])[C:15]=1[F:23]

Participants

7

Reactant 4

HCID 962WaterHCID 122241,2-DiiodoethaneHCID 11462508(4'-Bromo-2,3,2'-trifluorobiphenyl-4-yl)trimethylsilaneHCID 178418339Butyllithium

Product 1

HCID 11304300Trimethyl(2,3,2'-trifluoro-4'-iodobiphenyl-4-yl)silaneYield 84%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 15413tert-Butyl methyl etherSolvent

Procedure

30 ml (48 mmol) of 1.6 M BuLi are added dropwise at −78° C. to a solution of 15.8 g (44 mmol) of 7 in 132 ml of dry THF. After 15 minutes, 16 g (57.2 mmol) of 1,2-diiodoethane are added as solid, and the mixture is allowed to warm to room temperature over the course of 1 hour. Water and methyl tert-butyl ether are subsequently added. The organic phase is washed with water, sat. Na2S2O5 and sat. NaCl, dried over MgSO4 and filtered through SiO2. The solvent is removed under reduced pressure, petroleum ether is added to the oily residue, and the product is recrystallised at −25° C. (yield: 84%, m.p. 76.0° C.).

Workup

  1. washThe organic phase is washed with water, sat. Na2S2O5 and sat. NaCl
  2. dry with materialdried over MgSO4
  3. filtrationfiltered through SiO2
  4. customThe solvent is removed under reduced pressure, petroleum ether
  5. additionis added to the oily residue
  6. customthe product is recrystallised at −25° C. (yield: 84%, m.p. 76.0° C.)

Sources & evidence

ORD record
ord-422ed40b8542448883b6768c454c4bcb
Source dataset
uspto-grants-2012_02
Patent number
US08124817B2

Reaction notes

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