2-Bromobenzaldehyde → HCID 12715432, compound

HRID 1788473Notes

Reaction equation

HRID 1788473 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]=1

Participants

3

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

  1. additionwas added to a flame
  2. customdried flask
  3. customflushed with argon
  4. customwas reduced to −10° C.
  5. additionbenzylmagnesium chloride was slowly added to the flask via syringe
  6. stirringstirred at room temperature for 16 hours
  7. additionpoured over ice
  8. extractionIt was then extracted with ether (3×40 mL)
  9. customevaporated
  10. 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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