Hydrochloric Acid → 3,4-Dibromo-6-ethoxy-2-fluorophenol

HRID 1295942Notes

Reaction equation

HRID 1295942 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([O:8][CH2:9][CH3:10])[C:5]([O:11]CC)=[C:4]([F:14])[C:3]=1[Br:15].[Cl-].[Al+3].[Cl-].[Cl-].Cl>ClCCl>[Br:15][C:3]1[C:4]([F:14])=[C:5]([OH:11])[C:6]([O:8][CH2:9][CH3:10])=[CH:7][C:2]=1[Br:1]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 6451240Aluminum(III) ChlorideHCID 117098891,2-Dibromo-4,5-diethoxy-3-fluorobenzene

Product 1

HCID 229297133,4-Dibromo-6-ethoxy-2-fluorophenolYield 94%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

After dissolving 1,2-dibromo-3-fluoro-4,5-diethoxybenzene (5 g, 14.5 ml) in dichloromethane (70 ml), aluminum chloride (3.9 g, 29.3 mmol) was added while stirring on ice. The mixture was stirred at room temperature for 2 hours 30 minutes, 1 N hydrochloric acid (70 ml) was added and extraction was performed with ethyl acetate (70 ml×2) and then after washing the combined organic layers with brine (50 ml) and drying over anhydrous magnesium sulfate, the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (solvent: n-hexane-ethyl acetate) to obtain the title compound (4.31 g, 94%).

Workup

  1. additionwas added
  2. stirringThe mixture was stirred at room temperature for 2 hours 30 minutes
  3. extractionextraction
  4. washafter washing the combined organic layers with brine (50 ml)
  5. dry with materialdrying over anhydrous magnesium sulfate
  6. distillationthe solvent was distilled off under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (solvent: n-hexane-ethyl acetate)

Sources & evidence

ORD record
ord-0be36d6136644554a603f7eb634c225e
Source dataset
uspto-grants-2007_07
Patent number
US07244730B2

Reaction notes

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