Sodium Carbonate → 5366-51-8

HRID 1674733Notes

Reaction equation

HRID 1674733 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([OH:11])=[O:10])=[C:4]([F:12])[CH:3]=1.[C:13]1(B(O)O)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C([O-])([O-])=O.[Na+].[Na+]>O.CC(O)C.O.[OH-].[Na+]>[C:13]1([C:2]2[CH:7]=[CH:6][C:5]([CH2:8][C:9]([OH:11])=[O:10])=[C:4]([F:12])[CH:3]=2)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

7

Reactant 3

HCID 10340Sodium CarbonateHCID 66827Phenylboronic AcidHCID 140537922-(4-Bromo-2-fluorophenyl)acetic acid

Product 1

HCID 463147995366-51-8

Reagents, catalysts & solvents 3

HCID 962WaterSolvent2×HCID 14798Sodium HydroxideSolventHCID 21889133Propan-2-ol--water (1/1)Solvent2×

Conditions

Temperature
67.5 °C

Procedure

4-Bromo-2-fluoro-phenylacetic acid (0.25 gm, 1.1 mmole), phenylboronic acid (0.15 gm, 1.2 mmole) and 50% water wet 10% Palladium carbon (0.07 gm, 0.033 mmole Pd) were added to 10 ml of 5:1 water isopropanol mixture, then Na2CO3 (0.14 gm, 1.3 mmole) dissolved in 3 ml of water was added to the above mixture, the reaction was heated at 65-70° C. overnight, the reaction was cooled to room temperature, diluted with 20 ml of 70:15:1 i-PrOH/H2O/10% NaOH, filtered, the catalyst was washed with 20 ml×3 using the above mixture, the filtrate was acidified using 20% H2SO4, filtered and dried (0.2 gm, 83%) H1-NMR INOVA-500 (DMSO d6) δ 3.675 (s, 2H), 7.382-7.518 (m, 6H), 7.707 (d, J=7.5 Hz, 2H), 12.498 (s, 1H).

Workup

  1. additionwas added to the above mixture
  2. temperaturethe reaction was cooled to room temperature
  3. filtrationfiltered
  4. washthe catalyst was washed with 20 ml×3 using the above mixture
  5. filtrationfiltered
  6. dry with materialdried (0.2 gm, 83%) H1-NMR INOVA-500 (DMSO d6) δ 3.675 (s, 2H), 7.382-7.518 (m, 6H), 7.707 (d, J=7.5 Hz, 2H), 12.498 (s, 1H)

Sources & evidence

ORD record
ord-477a857fea8a40cca5237709bdc08ee2
Source dataset
uspto-grants-2011_08
Patent number
US08003641B2

Reaction notes

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