Ethyl Bromide → Methyl 2-ethoxy-2'-methyl-[1,1'-biphenyl]-4-carboxylate

HRID 2410535Notes

Reaction equation

HRID 2410535 reaction equation
[OH:1][C:2]1[CH:7]=[C:6]([C:8]([O:10][CH3:11])=[O:9])[CH:5]=[CH:4][C:3]=1[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[CH3:18].C(=O)([O-])[O-].[K+].[K+].[CH2:25](Br)[CH3:26]>C(#N)C>[CH2:25]([O:1][C:2]1[CH:7]=[C:6]([C:8]([O:10][CH3:11])=[O:9])[CH:5]=[CH:4][C:3]=1[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[CH3:18])[CH3:26]

Participants

5

Reactant 3

HCID 6332Ethyl BromideHCID 11430Potassium CarbonateHCID 58554208Methyl 2-hydroxy-2'-methyl-[1,1'-biphenyl]-4-carboxylate

Product 1

HCID 58554138Methyl 2-ethoxy-2'-methyl-[1,1'-biphenyl]-4-carboxylateYield 98.8%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
50 °C

Procedure

To a stirred solution of methyl 2-hydroxy-2′-methyl-1,1′-biphenyl-4-carboxylate (10 g, 41.2 mmol) in anhydrous ACN (100 mL) was added anhydrous potassium carbonate (17.1 g, 123.6 mmol) followed by ethyl bromide (15.4 mL, 206 mmol). The reaction mixture was heated at 50° C. for 48 hours, and then cooled to RT and filtered. The filtrate was concentrated under vacuum affording of the title compound as brown liquid (11 g, 98%). 1H-NMR (DMSO-d6, 400 MHz) δ 7.70 (d, 1H), 7.62 (s, 1H), 7.16-7.29 (m, 5H), 4.09 (q, 2H), 3.95 (s, 3H), 2.15 (s, 3H), 1.30 (t, 3H).

Workup

  1. temperaturecooled to RT
  2. filtrationfiltered
  3. concentrationThe filtrate was concentrated under vacuum

Sources & evidence

ORD record
ord-083d9ffd94c1458f99552979314021df
Source dataset
uspto-grants-2014_08
Patent number
US08815919B2

Reaction notes

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