Methyl 4-(bromomethyl)benzoate → 2-(4-Carbomethoxyphenyl)-1-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthyl)ethanone

HRID 1614095Notes

Reaction equation

HRID 1614095 reaction equation
[CH3:1][C:2]1([CH3:17])[CH2:11][CH2:10][C:9]([CH3:13])([CH3:12])[C:8]2[CH:7]=[C:6]([C:14](Cl)=[O:15])[CH:5]=[CH:4][C:3]1=2.Br[CH2:19][C:20]1[CH:29]=[CH:28][C:23]([C:24]([O:26][CH3:27])=[O:25])=[CH:22][CH:21]=1>C(COC)OC.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[Zn]>[C:24]([C:23]1[CH:28]=[CH:29][C:20]([CH2:19][C:14]([C:6]2[CH:5]=[CH:4][C:3]3[C:2]([CH3:17])([CH3:1])[CH2:11][CH2:10][C:9]([CH3:13])([CH3:12])[C:8]=3[CH:7]=2)=[O:15])=[CH:21][CH:22]=1)([O:26][CH3:27])=[O:25]

Participants

6

Reactant 2

HCID 256687Methyl 4-(bromomethyl)benzoateHCID 27954665,5,8,8-Tetramethyl-5,6,7,8-tetrahydronaphthalene-2-carbonyl chloride

Product 1

HCID 147264952-(4-Carbomethoxyphenyl)-1-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthyl)ethanone

Reagents, catalysts & solvents 3

HCID 23994ZincCatalystHCID 178418476HCID 178418476, compoundCatalystHCID 80711,2-DimethoxyethaneSolvent2×

Procedure

A solution of 4 g (16 mmol) of 5,6,7,8-tetrahydro-5,5,8,8-tetramethylnaphthalene-2-carbonyl chloride and 4 g (16 mmol) of methyl 4-bromomethylbenzoate in 20 ml of dimethoxyethane was added dropwise to a solution or suspension of 0.56 g of bis(triphenylphosphine)palladium(II) dichloride and 2.1 g of zinc powder in 40 ml of dimethoxyethane at room temperature. The reaction mixture was then refluxed for 6 h. After cooling, solids were filtered off and the filtrate was heated with active carbon and filtered hot. The filtrate was concentrated and yielded after recrystallization 3× from methanol and finally from isopropanol 0.9 g of the title compound of melting point 103°-104° C.

Workup

  1. temperatureThe reaction mixture was then refluxed for 6 h
  2. temperatureAfter cooling
  3. filtrationsolids were filtered off
  4. temperaturethe filtrate was heated with active carbon
  5. filtrationfiltered hot
  6. concentrationThe filtrate was concentrated
  7. customyielded
  8. customafter recrystallization 3× from methanol

Sources & evidence

ORD record
ord-559cf94ba15743f9b524eafb19affb8b
Source dataset
uspto-grants-1993_03
Patent number
US05194664

Reaction notes

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