2,6-dichloro-3-methoxybenzaldehyde

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

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

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

Procedure: Dissolve 2,6-dichloro-3-methoxy-benzaldehyde (10 g, 48.8 mmol) in ethanol (330 ml) add sodiumborohydride (1.8 g, 48.8 mmol) and stir at room temperature over night. Partition reaction mixture between water and ethyl acetate separate layers wash organic with brine, dry over sodium sulfate, filter and concentrate to yield 9.43 g (93%) of (2,6-Dichloro-3-methoxy-phenyl)-methanol. Partition reaction mixture between water and ethyl acetate separate layers wash organic with brine dry over sodium sulfate filter concentrate

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

Procedure: Dissolve 2,6-dichloro-3-methoxy-benzaldehyde (10 g, 48.8 mmol) in ethanol (330 ml) add sodiumborohydride (1.8 g, 48.8 mmol) and stir at room temperature over night. Partition reaction mixture between water and ethyl acetate separate layers wash organic with brine, dry over sodium sulfate, filter and concentrate to yield 9.43 g (93%) of (2,6-Dichloro-3-methoxy-phenyl)-methanol. Partition reaction mixture between water and ethyl acetate separate layers wash organic with brine dry over sodium sulfate filter concentrate

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

Procedure: Dissolve 2,6-dichloro-3-methoxy-benzaldehyde (10 g, 48.8 mmol) in ethanol (330 ml) add sodiumborohydride (1.8 g, 48.8 mmol) and stir at room temperature over night. Partition reaction mixture between water and ethyl acetate separate layers wash organic with brine, dry over sodium sulfate, filter and concentrate to yield 9.43 g (93%) of (2,6-Dichloro-3-methoxy-phenyl)-methanol. Partition reaction mixture between water and ethyl acetate separate layers wash organic with brine dry over sodium sulfate filter concentrate

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

Procedure: Dissolve 2,6-dichloro-3-hydroxy-benzaldehyde (10.7 g, 56 mmol) in N,N-dimethylformamide (80 ml), add potassium carbonate (15 g, 112 mmol), cesium carbonate(18.3 g, 56 mmol), iodomethane (7 ml, 112 mmol) and stir over night at room temperature. Filter reaction mixture into water washing solids with DMF, extract filtrate with ethyl acetate wash with water, brine, dry over sodium sulfate, filter and concentrate to yield 10 g (87%) of 2,6-dichloro-3-methoxy-benzaldehyde. Filter reaction mixture into water washing solids with DMF extract filtrate with ethyl acetate wash with water, brine dry over sodium sulfate filter concentrate

Conditions: temp:-78.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Dissolve tert-Butyl-(2,4-dichloro-phenoxy)-dimethyl-silane (48.4 g, 175 mmol) in tetrahydrofuran (575ml) and cool to −78° C. Add sec-butyl lithium (1.4M, 131 ml, 183 mmol) slowly at −78° C. and stir at −78° C. for 30 minutes. Add N,N-dimethylformamide and stir at −78° C. for 1.5 hours. Pour reaction mixture into acetic acid in water (1:12, 830 ml) and stir warming to room temperature. Extract with ether, wash with water, brine dry over sodium sulfate, filter and concentrate to yield a mixture of the title compound and TBS protected analog. Slur in hexanes and filter to yield 15 g (45%) of 2,6-dichloro-3-hydroxy-benzaldehyde. Pour warming to room temperature Extract with ether wash with water, brine dry over sodium sulfate filter concentrate to yield