Water → 2-Methyl-7-phenylnaphthalene

HRID 2105744Notes

Reaction equation

HRID 2105744 reaction equation
Br[C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][C:6]([CH3:12])=[CH:7][CH:8]=2)[CH:3]=1.[Li][C:14]1[CH:15]=[CH:16]C=[CH:18][CH:19]=1.O.[CH3:21]COCC>Cl[Ni]1(Cl)[P](C2C=CC=CC=2)(C2C=CC=CC=2)CCC[P]1(C1C=CC=CC=1)C1C=CC=CC=1>[CH3:21][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][C:6]([C:12]3[CH:16]=[CH:15][CH:14]=[CH:19][CH:18]=3)=[CH:7][CH:8]=2)[CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 3283Diethyl EtherHCID 153213362-Bromo-7-methylnaphthaleneHCID 178506676HCID 178506676, compound

Product 1

HCID 123530172-Methyl-7-phenylnaphthalene

Reagents, catalysts & solvents 1

HCID 178418745HCID 178418745, compoundCatalyst

Procedure

Solution of 2-bromo-7-methylnaphthalene (10 g, 45 mmole) in ether (100 ml) was cooled to −0° C., and Ni(dppp)Cl2 and solution of PhLi (obtained from 1.3 g of Mg and 5.6 ml of PhBr in 55 ml of ether) were added subsequently. Reaction mixture was allowed to warm to room temperature, stirred for additional 4 h with heating, cooled room temperature, stirred for additional 16 h, and treated by water (100 ml). Organic layer was separated, water layer was extracted by ether (3×50 ml). Combined organic fraction was evaporated, giving practically pure solid product. The yield 9.23 g (94%).

Workup

  1. customReaction mixture
  2. temperaturewith heating
  3. temperaturecooled room temperature
  4. stirringstirred for additional 16 h
  5. customOrganic layer was separated
  6. extractionwater layer was extracted by ether (3×50 ml)
  7. customCombined organic fraction was evaporated
  8. customgiving practically pure solid product

Sources & evidence

ORD record
ord-cebdd5ffeea74035981f44be2604aa61
Source dataset
uspto-grants-2009_08
Patent number
US07579417B2

Reaction notes

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