Toluene → HCID 39359537, compound

HRID 1626750Notes

Reaction equation

HRID 1626750 reaction equation
C1(C)C=CC=CC=1.C(=O)([O-])[O-].[Na+].[Na+].Br[C:15]1[CH:16]=[C:17]([CH:25]=[CH:26][CH:27]=1)[O:18][CH2:19][C:20]([O:22]CC)=[O:21].[CH3:28][O:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=1B(O)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.O.C(OCC)(=O)C.CO>[CH3:28][O:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=1[C:15]1[CH:27]=[CH:26][CH:25]=[C:17]([O:18][CH2:19][C:20]([OH:22])=[O:21])[CH:16]=1

Participants

9

Reactant 4

HCID 1140TolueneHCID 10340Sodium CarbonateHCID 27339582-Methoxyphenylboronic acidHCID 5197439Ethyl 2-(3-bromophenoxy)acetate

Product 1

HCID 39359537HCID 39359537, compoundYield 58.2%

Reagents, catalysts & solvents 4

HCID 178418397HCID 178418397, compoundCatalystHCID 887MethanolSolventHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

Under an Ar atmosphere, 12 mL of toluene, 3 mL of methanol, and 3 mL of 2M aqueous sodium carbonate solution were added to 500 mg (1.93 mmol) of ethyl (3-bromophenoxy)acetate and 352 mg (2.32 mmol) of (2-methoxyphenyl)boronic acid, and the mixture was degassed. Further, 112 mg (0.097 mmol) of tetrakis(triphenylphosphine)palladium(0) was added thereto, and the mixture was heated under stirring at 80° C. for 6 hours. After the mixture was cooled to room temperature, ethyl acetate and water were added thereto to separate the mixture. The water layer was separated, and filtration was performed. Thereafter, acidification was performed with 1N hydrochloric acid, and extraction with ethyl acetate was performed. The organic layer was washed with saturated saline and dried over anhydride magnesium sulfate, followed by filtration and condensation, thereby giving 290 mg of [(2′-methoxybiphenyl-3-yl)oxy]acetic acid (yield: 58%).

Workup

  1. customthe mixture was degassed
  2. temperaturethe mixture was heated
  3. temperatureAfter the mixture was cooled to room temperature
  4. customto separate the mixture
  5. customThe water layer was separated
  6. filtrationfiltration
  7. extractionThereafter, acidification was performed with 1N hydrochloric acid, and extraction with ethyl acetate
  8. washThe organic layer was washed with saturated saline
  9. dry with materialdried over anhydride magnesium sulfate
  10. filtrationfollowed by filtration and condensation

Sources & evidence

ORD record
ord-b8613a952c0d4ab0a39a0d825367a162
Source dataset
uspto-grants-2014_07
Patent number
US08785473B2

Reaction notes

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