Potassium Carbonate → 4'-Ethynyl-2-(trifluoromethyl)biphenyl

HRID 710443

Reaction equation

HRID 710443 reaction equation
[F:1][C:2]([F:18])([F:17])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[CH:14]=[CH:13][C:12]([CH:15]=O)=[CH:11][CH:10]=1.[C:19]([O-])([O-])=O.[K+].[K+].[N+](=C(P(=O)(OC)OC)C(=O)C)=[N-]>CO>[C:15]([C:12]1[CH:13]=[CH:14][C:9]([C:4]2[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=2[C:2]([F:18])([F:17])[F:1])=[CH:10][CH:11]=1)#[CH:19]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 13926532'-TrifluoroMethyl-Biphenyl-4-CarbaldehydeHCID 136023029(1E)-1-diazo-1-dimethoxyphosphorylpropan-2-one

Product 1

HCID 866618064'-Ethynyl-2-(trifluoromethyl)biphenylYield 85.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

To a stirred suspension of the product of Example 36, Step A, (0.21 g, 1 mmol) and K2CO3 (0.166 g, 1.1 mmol) in anhydrous MeOH (5 mL) was added a solution of dimethyl 1-diazo-2-oxopropylphosphonate (0.212 g, 1.1 mmol) in anhydrous MeOH (1 ml) and the mixture was stirred overnight at room temperature. The solvent was evaporated to dryness and the residue was diluted to 50 ml with EtOAc and washed with H2O. The organic layer was separated, dried over MgSO4, and filtered. The filtrate was passed through silica gel bead. The filtrate was evaporated to dryness to give the product (0.21 g, 85.4%), as creamy paste, which was used as such in next step. 1H-NMR (CDCl3) 3.11 (s, 1H); 7.25-7.31 (m, 3H); 7.44-7.55 (m, 4H); 7.73 (d, 1H, J=7.69 Hz).

Workup

  1. customThe solvent was evaporated to dryness
  2. additionthe residue was diluted to 50 ml with EtOAc
  3. washwashed with H2O
  4. customThe organic layer was separated
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. customThe filtrate was evaporated to dryness

Sources & evidence

ORD record
ord-bd7229f3ebbe4683b508cd737f42bc88
Source dataset
uspto-grants-2015_11
Patent number
US09181182B2

Linked notes

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