Sodium Carbonate → 4-(2-Acetylphenyl)benzoic acid

HRID 2244247Notes

Reaction equation

HRID 2244247 reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][C:7](B(O)O)=[CH:6][CH:5]=1)([OH:3])=[O:2].Br[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[C:20](=[O:22])[CH3:21].C(=O)([O-])[O-].[Na+].[Na+]>C(#N)C.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:20]([C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=1[C:7]1[CH:8]=[CH:9][C:4]([C:1]([OH:3])=[O:2])=[CH:5][CH:6]=1)(=[O:22])[CH3:21]

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 750602'-BromoacetophenoneHCID 3121834-Carboxyphenylboronic Acid

Product 1

HCID 200999564-(2-Acetylphenyl)benzoic acidYield 91%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 6342AcetonitrileSolvent

Conditions

Temperature
90 °C

Procedure

To a suspension of 4-carboxybenzeneboronic acid (2.0 g, 12.1 mmol) and 1-(2-bromo-phenyl)-ethanone (1.63 mL, 12.1 mmol) in dry acetonitrile (60 mL) was added a 0.4 M aqueous sodium carbonate solution (60 mL) and the reaction mixture purged with nitrogen for 10 minutes. Tetrakis(triphenylphosphine)palladium(0) (0.5 g, 0.433 mmol) was then added and the reaction mixture heated to 90° C. for 22 hours. The hot reaction mixture was filtered through celite and then concentrated in vacuo to remove acetonitrile. The resulting aqueous suspension was diluted with water to 75 mL then washed with diethyl ether (75 mL). The aqueous phase was acidified to pH 1 by the addition of concentrated hydrochloric acid and the resulting white suspension cooled to 4° C. for 1 hour. The solid product was filtered, washed with water and then dried in vacuo at 50° C. overnight to afford the title compound (2.62 g, 91%) as a white solid, m.p. 199-201° C.

Workup

  1. customthe reaction mixture purged with nitrogen for 10 minutes
  2. filtrationThe hot reaction mixture was filtered through celite
  3. concentrationconcentrated in vacuo
  4. customto remove acetonitrile
  5. additionThe resulting aqueous suspension was diluted with water to 75 mL
  6. washthen washed with diethyl ether (75 mL)
  7. additionThe aqueous phase was acidified to pH 1 by the addition of concentrated hydrochloric acid
  8. temperaturethe resulting white suspension cooled to 4° C. for 1 hour
  9. filtrationThe solid product was filtered
  10. washwashed with water
  11. customdried in vacuo at 50° C. overnight

Sources & evidence

ORD record
ord-3b4215882d5c4d8eb75d58dff4a2f144
Source dataset
uspto-grants-2010_03
Patent number
US07678787B2

Reaction notes

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