HCID 59832526, compound → HCID 12162325, compound

HRID 605031Notes

Reaction equation

HRID 605031 reaction equation
[F:1][C:2]([F:16])([F:15])[C:3]1[CH:4]=[C:5]([Mg]Br)[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1.Br[C:18]1[C:26]([CH3:27])=[CH:25][CH:24]=[C:23]2[C:19]=1[CH:20]=[C:21]([CH3:43])[CH:22]2[Si:28]([CH:31]1[C:39]2[C:34](=[C:35](Br)[C:36]([CH3:40])=[CH:37][CH:38]=2)[CH:33]=[C:32]1[CH3:42])([CH3:30])[CH3:29]>C1COCC1.[Cl-].[Cl-].[Zn+2].CC(C)([P](C(C)(C)C)([Pd][P](C(C)(C)C)(C(C)(C)C)C(C)(C)C)C(C)(C)C)C>[F:1][C:2]([F:16])([F:15])[C:3]1[CH:4]=[C:5]([C:18]2[C:26]([CH3:27])=[CH:25][CH:24]=[C:23]3[C:19]=2[CH:20]=[C:21]([CH3:43])[CH:22]3[Si:28]([CH:31]2[C:39]3[C:34](=[C:35]([C:5]4[CH:6]=[C:7]([C:9]([F:12])([F:10])[F:11])[CH:8]=[C:3]([C:2]([F:1])([F:16])[F:15])[CH:4]=4)[C:36]([CH3:40])=[CH:37][CH:38]=3)[CH:33]=[C:32]2[CH3:42])([CH3:30])[CH3:29])[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1

Participants

6

Reactant 2

HCID 59832526HCID 59832526, compoundHCID 178506227HCID 178506227, compound

Product 1

HCID 12162325HCID 12162325, compound

Reagents, catalysts & solvents 3

HCID 3007855ZincchlorideCatalystHCID 178418851HCID 178418851, compoundCatalystHCID 8028TetrahydrofuranSolvent4×

Procedure

In an argon atmosphere, to a solution of 15 mL of THF with 29.0 ml of 0.5 M ZnCl2 (14.5 mmol) in THF, 13.0 ml of 1.0 M 3,5-bis(trifluoromethyl) phenylmagnesium bromide (13.0 mmol) in THF was added at ambient temperature. This mixture was stirred for 1 hour, and, then, 10.0 ml of 0.02 M Pd(PtBu3)2 (0.20 mmol, 4 mol. %) in THF and 2.51 g (5.0 mmol) of 2 were added. The resulting mixture was stirred for 5 hours at reflux. The product was isolated by flash chromatography on Silica Gel 60 (40-63 μm, d 30 mm, l 100 mm; eluent: hexanes). Yield 3.65 g (95%) of white solid of ca. 1 to 1 mixture of rac- and meso-compounds.

Workup

  1. stirringThe resulting mixture was stirred for 5 hours
  2. temperatureat reflux
  3. customThe product was isolated by flash chromatography on Silica Gel 60 (40-63 μm, d 30 mm, l 100 mm; eluent: hexanes)

Sources & evidence

ORD record
ord-bd0e92a893684b3bbfb5e750b19e2cb6
Source dataset
uspto-grants-2011_03
Patent number
US07910783B2

Reaction notes

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