Chloropentafluorobenzene → Bis(pentafluorophenyl)diethoxysilane

HRID 856883

Reaction equation

HRID 856883 reaction equation
Cl[C:2]1[C:7]([F:8])=[C:6]([F:9])[C:5]([F:10])=[C:4]([F:11])[C:3]=1[F:12].[Li]C(CC)C.[CH2:18]([O:20][Si:21]([O:34][CH2:35][CH3:36])(Cl)[C:22]1[C:27]([F:28])=[C:26]([F:29])[C:25]([F:30])=[C:24]([F:31])[C:23]=1[F:32])[CH3:19]>CCOCC>[F:8][C:7]1[C:2]([Si:21]([C:22]2[C:23]([F:32])=[C:24]([F:31])[C:25]([F:30])=[C:26]([F:29])[C:27]=2[F:28])([O:34][CH2:35][CH3:36])[O:20][CH2:18][CH3:19])=[C:3]([F:12])[C:4]([F:11])=[C:5]([F:10])[C:6]=1[F:9]

Participants

5

Reactant 3

HCID 9579ChloropentafluorobenzeneHCID 21864267DiethoxychloropentafluorophenylsilaneHCID 178418400CID 53628100

Product 1

HCID 11102434Bis(pentafluorophenyl)diethoxysilane

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Conditions

Temperature
-70 °C

Procedure

39.52 g (0.195 mol) chloropentafluorobenzene is weighed to a 1000 mL vessel and 250 mL Et2O is added. The vessel is cooled down to −70° C. and 150 mL (0.195 mol) of sec-BuLi (1.3 M) is added dropwise during one hour. The temperature of the solution is kept below −50° C. all the time. The solution is stirred for 30 minutes and 62.54 g (0.195 mol) of diethoxychloropentafluorophenylsilane in Et2O (100 mL) is added in small portions. The solution is stirred for over night allowing it to warm up to room temperature. Formed clear solution is filtered and evaporated to dryness to result di(pentafluorophenyl)diethoxysilane, (C6F5)2Si(OEt)2.

Workup

  1. customis kept below −50° C.
  2. stirringThe solution is stirred for over night
  3. temperatureto warm up to room temperature
  4. customFormed clear solution
  5. filtrationis filtered
  6. customevaporated to dryness

Sources & evidence

ORD record
ord-4f127d6749d44c5f894daec6ee1cb876
Source dataset
uspto-grants-2006_12
Patent number
US07144827B2

Linked notes

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