Potassium Carbonate → HCID 59508382, compound

HRID 923681Notes

Reaction equation

HRID 923681 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][C:3]=1[F:9].C(=O)([O-])[O-].[K+].[K+].Br[CH2:17][CH:18]([O:22][CH2:23][CH3:24])[O:19][CH2:20][CH3:21]>CN(C)C=O>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH2:17][CH:18]([O:22][CH2:23][CH3:24])[O:19][CH2:20][CH3:21])=[CH:4][C:3]=1[F:9]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 74852Ethane, 2-bromo-1,1-diethoxy-HCID 27791534-Bromo-3-fluorophenol

Product 1

HCID 59508382HCID 59508382, compoundYield 101.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
135 °C

Procedure

4-Bromo-3-fluorophenol (7 g, 0.03665 mol) and potassium carbonate (7.6 g, 0.055 mol) were dissolved in N,N-dimethylformamide (9 mL). 2-Bromo-1,1-diethoxyethane (8.5 mL, 0.055 mol) was added and the reaction mixture was stirred and heated to 135° C. for 7 h. The solvent was removed after the reaction was completed. The residue was dissolved in ethyl acetate and washed with 2M NaOH solution. The organic phase was dried over Na2SO4. The solvent was evaporated to yield 1-bromo-4-(2,2-diethoxyethoxy)-2-fluorobenzene as an oil (11.4 g, 100%).

Workup

  1. customThe solvent was removed after the reaction
  2. dissolutionThe residue was dissolved in ethyl acetate
  3. washwashed with 2M NaOH solution
  4. dry with materialThe organic phase was dried over Na2SO4
  5. customThe solvent was evaporated

Sources & evidence

ORD record
ord-156b263cd3ea44b6909b36ece12ddffb
Source dataset
uspto-grants-2016_03
Patent number
US09278985B2

Reaction notes

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