HCID 90310712, compound → HCID 90310683, compound

HRID 1519176Notes

Reaction equation

HRID 1519176 reaction equation
Br[C:2]1[CH:15]=[CH:14][CH:13]=[C:12]([F:16])[C:3]=1[O:4][Si:5]([C:8]([CH3:11])([CH3:10])[CH3:9])([CH3:7])[CH3:6].[Br-].[CH:18]1([Zn+])[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]1>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.C1COCC1>[C:8]([Si:5]([O:4][C:3]1[C:12]([F:16])=[CH:13][CH:14]=[CH:15][C:2]=1[CH:18]1[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]1)([CH3:7])[CH3:6])([CH3:11])([CH3:10])[CH3:9]

Participants

5

Reactant 2

HCID 90310712HCID 90310712, compoundHCID 178418970HCID 178418970, compound

Product 1

HCID 90310683HCID 90310683, compound

Reagents, catalysts & solvents 2

HCID 178418851HCID 178418851, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A solution consisting of (2-bromo-6-fluorophenoxy)(tert-butyl)dimethylsilane (0.832 g, 2.73 mmol) and bis(tri-tert-butylphosphine)palladium(0) (0.070 g, 0.14 mmol) and dry THF (5 mL) was treated with cyclohexylzinc(II) bromide (7.0 mL, 3.5 mmol, 0.5 M in THF). The resultant mixture was heated for 45 minutes at 50° C., cooled to rt, and concentrated to dryness. The resultant residue was subjected to FCC purification to the title compound (0.841 g, 89%) which was used without purification.

Workup

  1. concentrationconcentrated to dryness
  2. customThe resultant residue was subjected to FCC purification to the title compound (0.841 g, 89%) which
  3. customwas used without purification

Sources & evidence

ORD record
ord-469800c64c944a35aaea63147b3f6589
Source dataset
uspto-grants-2015_07
Patent number
US09073876B2

Reaction notes

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