3-Bromobenzaldehyde → HCID 62608744, compound

HRID 898199Notes

Reaction equation

HRID 898199 reaction equation
[CH2:1]([Mg]Br)[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].[Br:9][C:10]1[CH:11]=[C:12]([CH:15]=[CH:16][CH:17]=1)[CH:13]=[O:14]>O1CCCC1>[Br:9][C:10]1[CH:17]=[CH:16][CH:15]=[C:12]([CH:13]([OH:14])[CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH3:6])[CH:11]=1

Participants

4

Reactant 2

HCID 765833-BromobenzaldehydeHCID 178444609HCID 178444609, compound

Product 1

HCID 62608744HCID 62608744, compoundYield 70.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Hexylmagnesium bromide (2.0M in THF, 3.7 mL, 7.4 mmol) was added to a solution of 3-bromobenzaldehyde (1.50 g, 8.11 mmol) in tetrahydrofuran (10 mL) at −78° C. After 10 min, the reaction was quenched by the addition of 2N hydrochloric acid (30 mL) and the product extracted into ethyl acetate (30 mL). The organic layer was washed with sat'd sodium chloride (25 mL), dried over magnesium sulfate and concentrated in vacuo. Silica gel chromatography eluting with 17% ethyl acetate/hexane gave 1.42 g (5.25 mmol, 65%) of product.

Workup

  1. customthe reaction was quenched by the addition of 2N hydrochloric acid (30 mL)
  2. extractionthe product extracted into ethyl acetate (30 mL)
  3. washThe organic layer was washed with sat'd sodium chloride (25 mL)
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated in vacuo
  6. washSilica gel chromatography eluting with 17% ethyl acetate/hexane

Sources & evidence

ORD record
ord-253e641013564813bf30edef1357d12c
Source dataset
uspto-grants-2008_04
Patent number
US07351725B2

Reaction notes

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