[2-(bromomethyl)phenyl]methanol

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 1.2 benzenedimethanol (1.41 g, 10 mmol), carbontetrabromide (3.648 g, 11 mmol), triphenylphosphine (2.885 g, 11 mmol) in dry methylene chloride (50 ml) was stirred at rt over 2 days under argon. The solvent was removed under reduced pressure and the residue chromotographed (flash silica gel, 1:1 t-butyl methyl ether: hexanes) to afford the title compound as a white solid. (0.99 g, 49%) The solvent was removed under reduced pressure

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 1.2 benzenedimethanol (1.41 g, 10 mmol), carbontetrabromide (3.648 g, 11 mmol), triphenylphosphine (2.885 g, 11 mmol) in dry methylene chloride (50 ml) was stirred at rt over 2 days under argon. The solvent was removed under reduced pressure and the residue chromotographed (flash silica gel, 1:1 t-butyl methyl ether: hexanes) to afford the title compound as a white solid. (0.99 g, 49%) The solvent was removed under reduced pressure

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 1.2 benzenedimethanol (1.41 g, 10 mmol), carbontetrabromide (3.648 g, 11 mmol), triphenylphosphine (2.885 g, 11 mmol) in dry methylene chloride (50 ml) was stirred at rt over 2 days under argon. The solvent was removed under reduced pressure and the residue chromotographed (flash silica gel, 1:1 t-butyl methyl ether: hexanes) to afford the title compound as a white solid. (0.99 g, 49%) The solvent was removed under reduced pressure

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a 3 neck 1-liter round bottomed flask equipped with a stirring bar, argon inlet, and pressure equalizing dropping funnel was added o-bromomethylbenzoic acid (35 g, 163 mmol) and 70 ml of dry tetrahydrofuran (THF). The slurry-solution was cooled in a 0° C. ice-salt bath and the dropping funnel was charged with a solution of borane in THF (212 ml of a 1.0 M solution, 212 mmol). This solution was added to the cold acid mixture, dropwise over 1 hour. When the addition was complete, the cooling bath was removed and the mixture was allowed to warm to room temperature and stir for 1 hour. The reaction was then quenched by careful addition of water (200 ml). The resulting solution was diluted with 600 ml of ether which resulted in a phase separation. The organic layer was separated and washed: H2O (2×500 ml) and brine (1×500 ml). Drying (MgSO4), filtration, and removal of the solvent in vacuo left 25 g of a solid which was recrystallized from boiling ethyl acetate-hexane to give the compound (1a): mp 61°-63° C.; 'H NMR (CDCl3) δ2.05 (s, 1H), 4.60 (s, 2H), 4.80 (s, 2H), 7.20-7.55 (m, 4H). To a 3 neck 1-liter round bottomed flask equipped with a stirring bar, argon inlet This solution was added to the cold acid mixture, dropwise over 1 hour When the addition the cooling bath was removed to warm to room temperature The reaction was then quenched by careful addition of water (200 ml) The resulting solution was diluted with 600 ml of ether which resulted in a phase separation The organic layer was separated washed Drying (MgSO4), filtration, and removal of the solvent in vacuo left 25 g of a solid which was recrystallized

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of the title compound of step (A) (10 g, 50 mmol) in CH2Cl2 (80 ml) cooled at 0° C. was added 2,6-lutidine (7.57 mL, 65 mmol), followed by dropwise addition of tert-butyldimethylsilyl trifluoromethanesulfonate (14.92 mL, 65 mmol). The reaction mixture was stirred at 0° C. for 45 minutes, then quenched with H2O (20 mL) and partitioned between EtOAc (450 mL) and H2O (150 mL). The organic layer was separated and washed with 10% NaHCO3 solution, brine (2×), dried (MgSO4) and concentrated in vacuo to give a yellow syrup, which was chromatographed eluting with 10-50% EtOAc/hexane to afford 13.89 g (88%) of the title compound of this step as a light yellow oil. quenched with H2O (20 mL) partitioned between EtOAc (450 mL) and H2O (150 mL) The organic layer was separated washed with 10% NaHCO3 solution, brine (2×) dried (MgSO4) concentrated in vacuo to give a yellow syrup, which was chromatographed eluting with 10-50% EtOAc/hexane

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of 1M BBr3 in CH2Cl2 (49.2 mL, 49.2 mmol) cooled at 0° C. was added dropwise over 45 minutes a solution of phthalan (17.40 g, 142.6 mmol) in CH2Cl2 (30 mL). After the addition, the mixture was heated to reflux (oil bath) for 1 hour, then cooled to room temperature and quenched with water (50 mL). The mixture was washed with H2O (100 mL), 50% saturated NaHCO3 (100 mL), H2O (100 mL), brine, dried (MgSO4) and concentrated in vacuo to give a brownish solid, which was crystallized from EtOAc/hexane to afford 16.442 g of the title compound of this step as a light yellow crystalline compound. The mother liquor was concentrated and the residue crystallized (EtOAc/hexane) to yield an additional 6.30 g of the title compound of this step (total amount of product: 22.742 g, 80% yield). After the addition the mixture was heated to reflux (oil bath) for 1 hour quenched with water (50 mL) The mixture was washed with H2O (100 mL), 50% saturated NaHCO3 (100 mL), H2O (100 mL), brine dried (MgSO4) concentrated in vacuo to give a brownish solid, which was crystallized from EtOAc/hexane

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 1,2 benzenedimethanol (1.41 g, 10 mmol), carbontetrabromide (3.648 g, 11 mmol), triphenylphosphine (2.885 g, 11 mmol) in dry methylene chloride (50 ml) was stirred at rt over 2 days under argon. The solvent was removed under reduced pressure and the residue chomatographed (flash silica gel, 1:1 t-butyl methyl ether: hexanes) to afford the title compound as a white solid. (0.99 g, 49%) The solvent was removed under reduced pressure

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 1,2 benzenedimethanol (1.41 g, 10 mmol), carbontetrabromide (3.648 g, 11 mmol), triphenylphosphine (2.885 g, 11 mmol) in dry methylene chloride (50 ml) was stirred at rt over 2 days under argon. The solvent was removed under reduced pressure and the residue chomatographed (flash silica gel, 1:1 t-butyl methyl ether:hexanes) to afford the title compound as a white solid. (0.99 g, 49%) The solvent was removed under reduced pressure

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 1.2 benzenedimethanol (1.41 g, 10 mmol), carbontetrabromide (3.648 g, 11 mmol), triphenylphosphine (2.885 g, 11 mmol) in dry methylene chloride (50 ml) was stirred at rt over 2 days under argon. The solvent was removed under reduced pressure and the residue chromotographed (flash silica gel, 1:1 t-butyl methyl ether: hexanes) to afford the title compound as a white solid. (0.99 g, 49%) The solvent was removed under reduced pressure