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

HRID 1630993Notes

Reaction equation

HRID 1630993 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 to afford of the title compound as brown liquid (11 g, 98%). 1H NMR (DMSO-d6, 400 MHz) δ 7.70 (1H, d), 7.62 (1H, s), 7.16-7.29 (5H, m), 4.09 (2H, q), 3.95 (3H, s), 2.15 (3H, s), 1.30 (3H, t).

Workup

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

Sources & evidence

ORD record
ord-8180313f134c46e7be0676d1374d025a
Source dataset
uspto-grants-2014_07
Patent number
US08791142B2

Reaction notes

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