Calcium Carbonate → 2-Bromo-5-fluorobenzyl alcohol

HRID 1859519Notes

Reaction equation

HRID 1859519 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): δ2.00 (t, 1 H), 4.72 (d, 2 H), 6.85-6.92 (m, 1 H), 7.26 (dd, 1 H), 7.48 (dd, 1 H).

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-ffa461c2e97642aeae7ca6e9cf136382
Source dataset
uspto-grants-2003_03
Patent number
US06528510B1

Reaction notes

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