1-Ethenyl-3-methylbenzene → HCID 19047738, compound

HRID 1780823Notes

Reaction equation

HRID 1780823 reaction equation
Br[C:2]1[CH:3]=[C:4]([CH:6]=[CH:7][CH:8]=1)[NH2:5].[CH3:9][C:10]1[CH:11]=[C:12]([CH:15]=[CH:16][CH:17]=1)[CH:13]=[CH2:14].C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C.C(N(CC)CC)C>CC([O-])=O.CC([O-])=O.[Pd+2].O.C(OCC)(=O)C>[CH3:9][C:10]1[CH:11]=[C:12](/[CH:13]=[CH:14]/[C:2]2[CH:3]=[C:4]([NH2:5])[CH:6]=[CH:7][CH:8]=2)[CH:15]=[CH:16][CH:17]=1

Participants

8

Reactant 4

HCID 75291-Ethenyl-3-methylbenzeneHCID 8471TriethylamineHCID 115623-BromoanilineHCID 80271Tri-o-tolylphosphine

Product 1

HCID 19047738HCID 19047738, compound

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 3-bromoaniline (545 uL), 3-methylstyrene (780 uL), tri(o-tolyl)phosphine (60 mg), Pd(OAc)2 (10 rag), and triethylamine (2.5 mL) was prepared in a sealed tube under argon atmosphere. The reaction was heated at 100° C. for 4 h, then cooled to room temperature and poured into ethyl acetate and water. The organic layer was washed with water and dried (Na2SO4), filtered, and concentrated in vacuo to provide the crude product. Purification by silica gel chromatography (20:1-5:1 hexane/EtOAc) provided the titled compound.

Workup

  1. customwas prepared in a sealed tube under argon atmosphere
  2. temperaturecooled to room temperature
  3. washThe organic layer was washed with water
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customto provide the crude product
  8. customPurification by silica gel chromatography (20:1-5:1 hexane/EtOAc)

Sources & evidence

ORD record
ord-0c53c29563a54a4f8e38fdbfefbbb87c
Source dataset
uspto-grants-1997_05
Patent number
US05631280

Reaction notes

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