Potassium Carbonate → 1-Fluoro-4-(2-methylbut-3-yn-2-yl)benzene

HRID 570678Notes

Reaction equation

HRID 570678 reaction equation
[N+](=[C:3](P(=O)(OC)OC)C(=O)C)=[N-].C([O-])([O-])=O.[K+].[K+].[F:19][C:20]1[CH:25]=[CH:24][C:23]([C:26]([CH3:30])([CH3:29])[CH:27]=O)=[CH:22][CH:21]=1>CO.CCOC(C)=O>[F:19][C:20]1[CH:25]=[CH:24][C:23]([C:26]([CH3:29])([C:27]#[CH:3])[CH3:30])=[CH:22][CH:21]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 820747502-(4-Fluorophenyl)-2-methylpropanalHCID 136023029(1E)-1-diazo-1-dimethoxyphosphorylpropan-2-one

Product 1

HCID 198258721-Fluoro-4-(2-methylbut-3-yn-2-yl)benzene

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

Next, a solution of dimethyl (1-diazo-2-oxopropyl)phosphonate (1.4 eq.) in MeOH (0.6 M) was treated at 0° C. with K2CO3 (2.4 eq.) and 2-(4-fluorophenyl)-2-methylpropanal (1.0 eq.). The reaction mixture was stirred for 1 hour, diluted with EtOAc, washed with water, dried (Na2SO4) and concentrated giving 1-fluoro-4-(2-methylbut-3-yn-2-yl)benzene: 1H NMR (600 MHz, CDCl3) δ 7.48-7.50 (m, 2 H), 6.97-7.00 (m, 2 H), 2.33 (s, 1 H), 1.57 (s, 6 H).

Workup

  1. washwashed with water
  2. dry with materialdried (Na2SO4)
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-beca74a66ecb4b9f8befce913a8e3ddd
Source dataset
uspto-grants-2015_05
Patent number
US09023864B2

Reaction notes

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