Sodium Carbonate → 4'-Cyano-2'-methylbiphenyl-4-carboxylic acid

HRID 399272Notes

Reaction equation

HRID 399272 reaction equation
Br[C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][C:3]=1[CH3:10].B([C:14]1[CH:22]=[CH:21][C:17]([C:18]([OH:20])=[O:19])=[CH:16][CH:15]=1)(O)O.C(=O)([O-])[O-].[Na+].[Na+]>COCCOC.O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[C:6]([C:5]1[CH:8]=[CH:9][C:2]([C:14]2[CH:22]=[CH:21][C:17]([C:18]([OH:20])=[O:19])=[CH:16][CH:15]=2)=[C:3]([CH3:10])[CH:4]=1)#[N:7]

Participants

7

Reactant 3

HCID 10340Sodium CarbonateHCID 3121834-Carboxyphenylboronic AcidHCID 27374944-Bromo-3-methylbenzonitrile

Product 1

HCID 218337684'-Cyano-2'-methylbiphenyl-4-carboxylic acidYield 69%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolvent

Procedure

A stirred solution of 4-bromo-3-methylbenzonitrile (5.0 g, 0.026 mole) and 4-boronobenzoic acid (4.2 g, 0.026 mole) in a mixture of DME (100 ml) and water (100 ml) under argon was treated with sodium carbonate (11.6 g, 0.11 mole) and tetrakis (triphenylphosphine) palladium (O) (0.55 g) and heated under reflux for 20 h. The solution was concentrated in vacuo to approx. 100 ml volume, then washed with ethyl acetate and acidified with 5M HCl acid. The solid which was produced was filtered off, washed with water and dried in vacuo to afford the title compound as a white solid (4.16 g, 69%).

Workup

  1. temperatureheated
  2. temperatureunder reflux for 20 h
  3. concentrationThe solution was concentrated in vacuo to approx. 100 ml volume
  4. washwashed with ethyl acetate
  5. customThe solid which was produced
  6. filtrationwas filtered off
  7. washwashed with water
  8. customdried in vacuo

Sources & evidence

ORD record
ord-02e21a61651b48e7a6e4cbff0827a6cb
Source dataset
uspto-grants-1998_10
Patent number
US05817833

Reaction notes

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