Calcium Carbonate → 2-Bromo-5-fluorobenzyl alcohol
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
Product 1
Reagents, catalysts & solvents 2
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
- temperatureThe mixture was heated
- temperatureto reflux overnight
- concentrationThe solution was concentrated
- customthe residue was partitioned between H2O and CH2Cl2
- washThe organic phase was washed with 1N HCl and brine
- dry with materialdried (MgSO4)
- filtrationfiltered
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-1076bffe427846ac8eb8c24fef4f4f01
- Source dataset
- uspto-grants-2005_02
- Patent number
- US06852711B2
Reaction notes
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