Acetic Acid → 3-Bromo-2-fluorophenol

HRID 19137Notes

Reaction equation

HRID 19137 reaction equation
[Br:1][C:2]1[C:3]([F:11])=[C:4](B(O)O)[CH:5]=[CH:6][CH:7]=1.C(O)(=[O:14])C.OO>O1CCCC1>[Br:1][C:2]1[C:3]([F:11])=[C:4]([OH:14])[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 784Hydrogen PeroxideHCID 16217170(3-Bromo-2-fluorophenyl)boronic acid

Product 1

HCID 184012573-Bromo-2-fluorophenolYield 89%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3-bromo-2-fluoro-phenylboronic acid (25.0 g, 0.114 mol) in tetrahydrofuran (250 mL) was added glacial acetic acid (150 mL). The resulting mixture was cooled to 0° C. before hydrogen peroxide (50% aqueous solution, 25 mL) was added. The resulting mixture was allowed to come to room temperature and stirred for 24 h. The mixture was evaporated and the residue was dissolved in ethyl acetate, washed with hydrochloric acid (0.5N), water and brine. The organic phase was dried, filtered and evaporated which afforded 3-bromo-2-fluoro-phenol (19.50 g, 89%) as a brown solid.

Workup

  1. additionwas added
  2. customto come to room temperature
  3. customThe mixture was evaporated
  4. dissolutionthe residue was dissolved in ethyl acetate
  5. washwashed with hydrochloric acid (0.5N), water and brine
  6. customThe organic phase was dried
  7. filtrationfiltered
  8. customevaporated which

Sources & evidence

ORD record
ord-ac7049d8162c4288ad45197553ae28bd
Source dataset
uspto-grants-2010_06
Patent number
US07741327B2

Reaction notes

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