Toluene → 6-Methoxy-5-(pentafluoroethyl)naphthalene-1-carbonitrile

HRID 620933Notes

Reaction equation

HRID 620933 reaction equation
[CH3:1][O:2][C:3]1[C:4](Br)=[C:5]2[C:10](=[CH:11][CH:12]=1)[C:9]([C:13]#[N:14])=[CH:8][CH:7]=[CH:6]2.C1(C)C=CC=CC=1.CN(C)C=O.[F:28][C:29]([F:37])([F:36])[C:30]([F:35])([F:34])C([O-])=O.[K+]>[Cu]I.C(Cl)Cl.O.C1(C)C=CC=CC=1.O>[CH3:1][O:2][C:3]1[C:4]([C:30]([F:35])([F:34])[C:29]([F:37])([F:36])[F:28])=[C:5]2[C:10](=[CH:11][CH:12]=1)[C:9]([C:13]#[N:14])=[CH:8][CH:7]=[CH:6]2

Participants

9

Reactant 4

HCID 1140TolueneHCID 6228DimethylformamideHCID 139590745-Bromo-6-methoxynaphthalene-1-carbonitrileHCID 23667659Propanoic acid, 2,2,3,3,3-pentafluoro-, potassium salt (1:1)

Product 1

HCID 139590756-Methoxy-5-(pentafluoroethyl)naphthalene-1-carbonitrile

Reagents, catalysts & solvents 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 22272177Toluene waterSolvent

Procedure

A suitable reaction vessel was charged with 8.1 g of 6-methoxy-5-bromo-1-cyanonaphthalene, 11.8 g of CuI, 35 ml of toluene, and 55 ml of N,N-dimethylformamide. The reaction mixture was heated to 165° C. with concurrent azeotropic removal of toluene/water (25 ml) and then maintained at 155° C. when 11.8 g of potassium pentafluoropropionate was added. The reaction was monitored by VPC. After five hours no starting material was detected and the reaction mixture was poured into 150 ml of water and 125 ml of methylene chloride. The two phases were filtered, after which the organic layer was separated, washed with brine, and concentrated in vacuo to provide a crude 6-methoxy-5-pentafluoroethyl-1-cyanonaphthalene (6-MPCN) having a purity of greater than 95%.

Workup

  1. additionwas added
  2. filtrationThe two phases were filtered
  3. customafter which the organic layer was separated
  4. washwashed with brine
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-205f2f7f05404ab588f95db684795dfc
Source dataset
uspto-grants-1989_04
Patent number
US04822904

Reaction notes

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