4-Bromobenzaldehyde → 1-(4-Bromophenyl)hexan-1-ol

HRID 734624

Reaction equation

HRID 734624 reaction equation
[CH2:1]([Mg]Br)[CH2:2][CH2:3][CH2:4][CH3:5].[Br:8][C:9]1[CH:16]=[CH:15][C:12]([CH:13]=[O:14])=[CH:11][CH:10]=1>C1COCC1>[Br:8][C:9]1[CH:16]=[CH:15][C:12]([CH:13]([OH:14])[CH2:1][CH2:2][CH2:3][CH2:4][CH3:5])=[CH:11][CH:10]=1

Participants

4

Reactant 2

HCID 707414-BromobenzaldehydeHCID 178445865HCID 178445865, compound

Product 1

HCID 126030861-(4-Bromophenyl)hexan-1-olYield 74%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

n-Pentyl magnesium bromide (2.0 M in THF, 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 h, the reaction was quenched with 3 N HCl and extracted with Et2O (3×120 mL). Combined extracts were washed with brine (100 mL), dried (Na2SO4), filtered and concentrated in vacuo. Purification of the residue by flash column chromatography on silica gel (5% EtOAc/Hex) afforded 5.1 g (74%) of 1-(4-bromophenyl)-hexan-1-ol.

Workup

  1. customthe reaction was quenched with 3 N HCl
  2. extractionextracted with Et2O (3×120 mL)
  3. washCombined extracts were washed with brine (100 mL)
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customPurification of the residue by flash column chromatography on silica gel (5% EtOAc/Hex)

Sources & evidence

ORD record
ord-c16b0269b13a415ba2dc85236b74787a
Source dataset
uspto-grants-2009_09
Patent number
US07592364B2

Linked notes

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