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16th September 2013 @ 11:27

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Reaction information

*#Reaction file
ReactionScheme.cdx
 
*Reaction file type CDX 
*Procedure

Sodium borohydroxide (1.08 g, 29.00 mmol, 1 equiv.) in several portions was added to a solution of 3-bromobenzaldehyde (10 mL, 86.00 mmol, 3 equiv.) in ethanol (100 mL) at 25 °C.  The mixture was stirred for 3 hours.

The reaction was quenched with water (80 mL) and the product was extracted into ethyl acetate (2 x 100 mL).  The ethyl acetate washes were combined and washed with brine (2 x 100 mL) before being dried over magnesium sulphate, filtered and concentrated under reduced pressure.

The product was purified by bulb to bulb distillation (26 mmHg, 200 °C) to yield the product (9.68 g, 52 mmol, 60 %).

*Yield (%) 60
*Type of Yield Isolated Product Yield 
Reference(s)

Callahan, J. F.; Lin, G.; Wan, Z.; Yan, H. WO2009/100166 A1, 2009

L.Sayerpp18-19.pdf
Further information Using the method of Callahan et al

For multistep reactions (or their steps):

Overall reaction? False 
For overall reaction - links to child reaction steps N/A 
For step in multistep reaction - link to previous reaction step N/A 
For step in multistep reaction - link to following reaction step Reaction 51
Attached Files
ReactionScheme.cdx
L.Sayerpp18-19.pdf