HCID 11270883, compound → HCID 22048150, compound

HRID 895231Notes

Reaction equation

HRID 895231 reaction equation
[C:1]([Si:5]([O:8][C:9]1[C:18]([Br:19])=[CH:17][C:16]2[C:11](=[C:12]([Cl:21])[CH:13]=[C:14](Br)[CH:15]=2)[CH:10]=1)([CH3:7])[CH3:6])([CH3:4])([CH3:3])[CH3:2].[CH3:22][O:23][C:24]1[CH:29]=[CH:28][C:27]([Mg]Br)=[CH:26][CH:25]=1>C1COCC1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[C:1]([Si:5]([O:8][C:9]1[C:18]([Br:19])=[CH:17][C:16]2[C:11](=[C:12]([Cl:21])[CH:13]=[CH:14][CH:15]=2)[C:10]=1[C:27]1[CH:28]=[CH:29][C:24]([O:23][CH3:22])=[CH:25][CH:26]=1)([CH3:7])[CH3:6])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 2

HCID 11270883HCID 11270883, compoundHCID 178491912HCID 178491912, compound

Product 1

HCID 22048150HCID 22048150, compoundYield 69%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A solution of tert-butyl[(3,6-dibromo-8-chloro-2-naphthyl)oxy]dimethylsilane (1.95 g, 4.32 mmol), 4-methoxyphenylmagnesium bromide (13.8 mL of 0.5 N solution, 6.9 mmol), and tetrakis(triphenylphosphine)palladium (0.25 g, 0.21 mmol) in THF (10 mL) were stirred at reflux for 8 hr. The reaction was quenched with water (100 mL) and extracted with ethyl acetate (3×150 mL). The combined organic layers were washed with water, dried with sodium sulfate, filtered, evaporation of the solvent, and purified on a silica column (5% ethyl acetate—hexanes) to yield 1.42 g (69%) of the title compound as a white solid: 1H NMR (CDCl3): δ 0.36 (6H, s), 1.10 (9H, s), 3.87 (3H, s), 7.01 (2H, d, J=8.78 Hz), 7.33(1H,d, J=1.36 Hz), 7.58 (2H, d, J=8.75 Hz), 7.73 (1H, s), 7.78 (1H, d, J=1.62 Hz), 8.10 (1H, s).

Workup

  1. temperatureat reflux for 8 hr
  2. customThe reaction was quenched with water (100 mL)
  3. extractionextracted with ethyl acetate (3×150 mL)
  4. washThe combined organic layers were washed with water
  5. dry with materialdried with sodium sulfate
  6. filtrationfiltered
  7. customevaporation of the solvent
  8. custompurified on a silica column (5% ethyl acetate—hexanes)

Sources & evidence

ORD record
ord-a1777f46200346789ec55d8b2c911d07
Source dataset
uspto-grants-2005_07
Patent number
US06914074B2

Reaction notes

Loading…