Potassium Carbonate → HCID 66617711, compound

HRID 1846043Notes

Reaction equation

HRID 1846043 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([OH:9])[CH:5]=[CH:6][C:7]=1[F:8].C(=O)([O-])[O-].[K+].[K+].[CH3:16][O:17][C:18]1[CH:25]=[CH:24][C:21]([CH2:22]Cl)=[CH:20][CH:19]=1>CN(C=O)C>[Br:1][C:2]1[CH:3]=[C:4]([O:9][CH2:22][C:21]2[CH:24]=[CH:25][C:18]([O:17][CH3:16])=[CH:19][CH:20]=2)[CH:5]=[CH:6][C:7]=1[F:8]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 699934-Methyloxybenzyl chlorideHCID 27833813-Bromo-4-Fluorophenol

Product 1

HCID 66617711HCID 66617711, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 3-bromo-4-fluorophenol (2.18 g, 11.4 mmol) in DMF (15 mL) was added potassium carbonate (3.15 g, 22.8 mmol) portion wise at room temperature. The mixture was stirred at room temperature for 10 minutes then 4-methoxybenzyl chloride (1.55 mL, 11.4 mmol) was added drop wise. On completion of the addition the reaction was heated at 60° C. under nitrogen for 15 hours. The cooled reaction mixture was quenched with water (50 mL) and extracted with EtOAc (3×50 mL). The combined extracts were washed with 1M aqueous NaOH solution (50 mL) and brine (50 mL), then dried over anhydrous MgSO4, filtered and concentrated in vacuo to afford the crude title compound as an off-white solid in quantitative yield, 3.62 g.

Workup

  1. additionOn completion of the addition the reaction
  2. temperaturewas heated at 60° C. under nitrogen for 15 hours
  3. customThe cooled reaction mixture
  4. customwas quenched with water (50 mL)
  5. extractionextracted with EtOAc (3×50 mL)
  6. washThe combined extracts were washed with 1M aqueous NaOH solution (50 mL) and brine (50 mL)
  7. dry with materialdried over anhydrous MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-0deb3bc2819a4238a8b9a3dd54808b7f
Source dataset
uspto-grants-2015_02
Patent number
US08952008B2

Reaction notes

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