Ethanol → 1,2-Diethoxy-3-fluorobenzene

HRID 2078528Notes

Reaction equation

HRID 2078528 reaction equation
[CH2:1]([O:3][C:4]1[C:9]([F:10])=[CH:8][CH:7]=[CH:6][C:5]=1[OH:11])[CH3:2].[OH-].[Na+].[CH2:14](O)[CH3:15].BrCC>ClCCl>[CH2:14]([O:11][C:5]1[CH:6]=[CH:7][CH:8]=[C:9]([F:10])[C:4]=1[O:3][CH2:1][CH3:2])[CH3:15]

Participants

6

Reactant 4

HCID 702Ethanol2×HCID 6332Ethyl BromideHCID 14798Sodium HydroxideHCID 545787312-Ethoxy-3-fluorophenol

Product 1

HCID 224601261,2-Diethoxy-3-fluorobenzeneYield 75%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
10 °C

Procedure

To a 250 ml reactor were added 12.5 (0.08 mol) of 2-ethoxy-3 -fluorophenol [F1], 3.2 g (0.08 mol) of sodium hydroxide and 20 ml of ethanol. After cooling to around 10° C., 20 ml of an ethanol solution of 9.6 g (0.088 ml) of bromoethane was slowly added. After the termination of the addition, they were reacted under a reflux temperature for 3 hours and, after the termination of the reaction, dichloromethane was added, followed by extraction. The extraction liquid was washed with water and dried, and the solvent was removed by distillation to obtain 11.0 g of an oily product [G1]. The process yield was 75%.

Workup

  1. additionAfter the termination of the addition, they
  2. customwere reacted under a reflux temperature for 3 hours
  3. additionwas added
  4. extractionfollowed by extraction
  5. extractionThe extraction liquid
  6. washwas washed with water
  7. customdried
  8. customthe solvent was removed by distillation

Sources & evidence

ORD record
ord-6c12492172ef48cda1f73699d651e1b6
Source dataset
uspto-grants-2011_04
Patent number
US07928268B2

Reaction notes

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