4-Bromobenzaldehyde → HCID 12603087, compound

HRID 734625Notes

Reaction equation

HRID 734625 reaction equation
[CH2:1]([Mg]Br)[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].[Br:9][C:10]1[CH:17]=[CH:16][C:13]([CH:14]=[O:15])=[CH:12][CH:11]=1>C1COCC1>[Br:9][C:10]1[CH:17]=[CH:16][C:13]([CH:14]([OH:15])[CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH3:6])=[CH:12][CH:11]=1

Participants

4

Reactant 2

HCID 707414-BromobenzaldehydeHCID 178444609HCID 178444609, compound

Product 1

HCID 12603087HCID 12603087, compoundYield 76.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

n-Hexyl magnesium bromide (2.0 M in Et2O, 27 mL, 54 mmol) was added to a solution of 4-bromobenzaldehyde (5.0 g, 27 mmol) in THF (20 mL) at 0° C. under nitrogen. After 1.5 h at 0° C., the reaction was quenched slowly with 3 N HCl (20 mL) and concentrated in vacuo. The residue was diluted with water (30 mL) and extracted with Et2O (3×150 mL). Combined extracts were dried (Na2SO4), filtered and concentrated in vacuo. Purification of the residue by flash column chromatography on silica gel (5%→10% EtOAc/Hex) afforded 5.6 g (76%) of 1-(4-bromophenyl)-heptan-1-ol.

Workup

  1. customthe reaction was quenched slowly with 3 N HCl (20 mL)
  2. concentrationconcentrated in vacuo
  3. additionThe residue was diluted with water (30 mL)
  4. extractionextracted with Et2O (3×150 mL)
  5. dry with materialCombined extracts were dried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customPurification of the residue by flash column chromatography on silica gel (5%→10% EtOAc/Hex)

Sources & evidence

ORD record
ord-90039679008e4cf9b5d66915d96cdfb8
Source dataset
uspto-grants-2009_09
Patent number
US07592364B2

Reaction notes

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