2-Bromobenzaldehyde → HCID 12715432, compound
Reaction equation
[Br:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]=[O:5]>C(OCC)C>[Br:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]([OH:5])[CH2:4][C:3]1[CH:6]=[CH:7][CH:8]=[CH:9][CH:2]=1Participants
3
Reactant 1
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -10 °C
Procedure
A mixture of 2-bromobenzaldehyde (1 mL, 5.4 mmol) in diethylether (2 mL) was added to a flame dried flask, and flushed with argon. The temperature was reduced to −10° C. and benzylmagnesium chloride was slowly added to the flask via syringe. The reaction was stirred at −10° C. for 1 hour and then stirred at room temperature for 16 hours. The reaction was the poured over ice and acidified to pH 3. It was then extracted with ether (3×40 mL). The organic layers were combined, evaporated, and the resulting residue was purified via silica gel chromatography to produce 520 mg (33% yield) of the title intermediate.
Workup
- additionwas added to a flame
- customdried flask
- customflushed with argon
- customwas reduced to −10° C.
- additionbenzylmagnesium chloride was slowly added to the flask via syringe
- stirringstirred at room temperature for 16 hours
- additionpoured over ice
- extractionIt was then extracted with ether (3×40 mL)
- customevaporated
- customthe resulting residue was purified via silica gel chromatography
Sources & evidence
- ORD record
- ord-6407c5c47c5d40179ff0ffbe2a0ddb91
- Source dataset
- uspto-grants-2009_03
- Patent number
- US07511145B2
Reaction notes
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