Ethanol → 1,2-Diethoxy-3-fluorobenzene

HRID 2078530Notes

Reaction equation

HRID 2078530 reaction equation
[F:1][C:2]1[CH:8]=[CH:7][CH:6]=[C:4]([OH:5])[C:3]=1[OH:9].[OH-].[Na+].[CH2:12](O)[CH3:13].Br[CH2:16][CH3:17]>ClCCl>[CH2:16]([O:5][C:4]1[CH:6]=[CH:7][CH:8]=[C:2]([F:1])[C:3]=1[O:9][CH2:12][CH3:13])[CH3:17]

Participants

6

Reactant 4

HCID 702Ethanol2×HCID 6332Ethyl BromideHCID 14798Sodium HydroxideHCID 677643-Fluorocatechol

Product 1

HCID 224601261,2-Diethoxy-3-fluorobenzeneYield 81%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
10 °C

Procedure

To a 500 ml flask were added 38.4 (0.3 mol) of 3-fluorocatechol [H], 12 g (0.3 mol) of sodium hydroxide and 100 ml of ethanol. After cooling to around 10° C., 100 ml of an ethanol solution of 76.3 g (0.7 mol) of bromoethane was slowly added. After the termination of the addition, they were reacted under a reflux temperature for 5 hours. 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 45.5 g of 1,2 -diethoxy-3-fluorobenzene [G1] as an oily product. The process yield was 81%.

Workup

  1. additionAfter the termination of the addition, they
  2. customwere reacted under a reflux temperature for 5 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-e43e40406ec24023b2445bdb3e7414ae
Source dataset
uspto-grants-2011_04
Patent number
US07928268B2

Reaction notes

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