Sodium Bicarbonate → HCID 23005037, compound

HRID 1470583Notes

Reaction equation

HRID 1470583 reaction equation
Br[CH2:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([O:15][CH3:16])[CH:10]=2)=[CH:5][C:4]=1[F:17].C(=O)(O)[O-:19].[Na+]>CS(C)=O>[F:17][C:4]1[CH:5]=[C:6]([C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([O:15][CH3:16])[CH:10]=2)[CH:7]=[CH:8][C:3]=1[CH:2]=[O:19]

Participants

4

Reactant 2

HCID 516892Sodium BicarbonateHCID 58073801HCID 58073801, compound

Product 1

HCID 23005037HCID 23005037, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 4-bromomethyl-3-fluoro-3′-methoxy-biphenyl (0.45 g, 1.5 mmol) in dimethyl sulfoxide (10 mL) was added sodium bicarbonate (1.79 g, 21.3 mmol) and the resulting mixture was then stirred at 100° C. for 2 h. After the reaction was completed, it was cooled to room temperature and quenched with brine solution. The mixture was extracted with diethylether (50 mL×2) and the combined ether layers were washed with water, dried over anhydrous sodium sulphate and concentrated. The resulting residue was purified by column chromatography using 4% ethyl acetate in hexane to obtain the title compound.

Workup

  1. temperatureit was cooled to room temperature
  2. customquenched with brine solution
  3. extractionThe mixture was extracted with diethylether (50 mL×2)
  4. washthe combined ether layers were washed with water
  5. dry with materialdried over anhydrous sodium sulphate
  6. concentrationconcentrated
  7. customThe resulting residue was purified by column chromatography

Sources & evidence

ORD record
ord-bca78862d8ce4c7e826caae6350ca7d7
Source dataset
uspto-grants-2015_04
Patent number
US09006454B2

Reaction notes

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