Triethylamine → HCID 10036923, compound

HRID 1378309Notes

Reaction equation

HRID 1378309 reaction equation
C[C:2]1[CH:7]=[CH:6][C:5](Br)=[CH:4][C:3]=1[CH3:9].[C:10]1(B(O)O)[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[CH:13]=[CH:12][CH:11]=1.[CH2:23](N(CC)CC)C>C([O-])(=O)C.C([O-])(=O)C.[Pd+2].C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C.CN(C)C=O>[CH3:23][C:5]1[CH:6]=[C:7]([C:10]2[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[CH:13]=[CH:12][CH:11]=2)[CH:2]=[C:3]([CH3:9])[CH:4]=1

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 685044-Bromo-o-xyleneHCID 2545321-Naphthaleneboronic acid

Product 1

HCID 10036923HCID 10036923, compoundYield 73%

Reagents, catalysts & solvents 3

HCID 80271Tri-o-tolylphosphineCatalystHCID 167845palladium(II) acetateCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of dimethyl-5-bromobenzene (1.85 g, 10 mmol), 1-naphthalene boronic acid (1.89 g, 11 mmol), triethylamine (2.8 mL, 20 mmol), tris-(2-tolyl)phosphine (0.125 g, 0.4 mmol), palladium (II) diacetate (0.045 g, 0.4 mmol) and anhydrous dimethylformamide (25 mL) with 5 Å molecular sieves (0.5 g) was stirred at 100° C. under a nitrogen atmosphere for about 4 hours. The solvent was evaporated in vacuo and the residue was treated with 5% aqueous ammonia solution, extracted with ethyl acetate, and washed with saturated aqueous sodium chloride. After filtration to remove a black precipitate, the organic layer was dried over magnesium sulfate, filtered and evaporated. The yellowish oil residue was chromatographed on silica gel (methylene chloride; petroleum ether 1:2 as eluant) to give a colorless oil (1.7 g, 7.3 mmol) in 73% yield. This crystallized upon standing (mp 68°-70° C.).

Workup

  1. customThe solvent was evaporated in vacuo
  2. additionthe residue was treated with 5% aqueous ammonia solution
  3. extractionextracted with ethyl acetate
  4. washwashed with saturated aqueous sodium chloride
  5. filtrationAfter filtration
  6. customto remove a black precipitate
  7. dry with materialthe organic layer was dried over magnesium sulfate
  8. filtrationfiltered
  9. customevaporated
  10. customThe yellowish oil residue was chromatographed on silica gel (methylene chloride; petroleum ether 1:2 as eluant)

Sources & evidence

ORD record
ord-e042d87403d041b39d4e7737c27d6343
Source dataset
uspto-grants-1997_09
Patent number
US05668121

Reaction notes

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