Calcium Carbonate → 2-Bromo-5-fluorobenzyl alcohol

HRID 23447

Reaction equation

HRID 23447 reaction equation
[Br:1][C:2]1[CH:9]=[CH:8][C:7]([F:10])=[CH:6][C:3]=1[CH2:4]Br.C([O-])([O-])=[O:12].[Ca+2]>O1CCOCC1.O>[Br:1][C:2]1[CH:9]=[CH:8][C:7]([F:10])=[CH:6][C:3]=1[CH2:4][OH:12]

Participants

5

Reactant 2

HCID 10112Calcium CarbonateHCID 5179721-Bromo-2-(bromomethyl)-4-fluorobenzene

Product 1

HCID 27733492-Bromo-5-fluorobenzyl alcohol

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

2-Bromo-5-fluorobenzylbromide (2.0 g, 7.46 mmol) was dissolved in dioxane (25 mL) and H2O (25 mL), and CaCO3 (3.84 g, 38.39 mmol) was added. The mixture was heated to reflux overnight. The solution was concentrated, and the residue was partitioned between H2O and CH2Cl2. The organic phase was washed with 1N HCl and brine, dried (MgSO4), filtered, and concentrated to afford the title compound. 1H NMR (CDCl3): δ 2.00 (t, 1H), 4.72 (d, 2H), 6.85-6.92 (m, 1H), 7.26 (dd, 1H), 7.48 (dd, 1H).

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux overnight
  3. concentrationThe solution was concentrated
  4. customthe residue was partitioned between H2O and CH2Cl2
  5. washThe organic phase was washed with 1N HCl and brine
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-1076bffe427846ac8eb8c24fef4f4f01
Source dataset
uspto-grants-2005_02
Patent number
US06852711B2

Linked notes

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