5-Bromo-2-chlorobenzaldehyde → 1-(5-Bromo-2-chlorophenyl)ethanol

HRID 858786Notes

Reaction equation

HRID 858786 reaction equation
[CH3:1][Li].[Br:3][C:4]1[CH:5]=[CH:6][C:7]([Cl:12])=[C:8]([CH:11]=1)[CH:9]=[O:10]>C1COCC1>[Br:3][C:4]1[CH:5]=[CH:6][C:7]([Cl:12])=[C:8]([CH:9]([OH:10])[CH3:1])[CH:11]=1

Participants

4

Reactant 2

HCID 106089255-Bromo-2-chlorobenzaldehydeHCID 178418348HCID 178418348, compound

Product 1

HCID 587626441-(5-Bromo-2-chlorophenyl)ethanolYield 91%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Methyl lithium (11.6 mL, 16.3 mmol, 1.4M in ether) was added to a cooled −78° C. solution of 5-bromo-2-chloro-benzaldehyde (2.75 g, 12.5 mmol) dissolved in THF (40 mL). The reaction mixture was stirred for 15 hours and then quenched with saturated NH4Cl and extracted with EtOAc. The organic extracts were washed with 1N HCl, brine, dried over Na2SO4 and concentrated to an oil. The oil was purified by flash column chromatography (0% to 10% EtOAc in hexanes) to give the title compound as a solid (2.63 g, 91%). 1H NMR (400 MHz, CDCl3): δ 6.32 (d, J=6.3 Hz, 3 H), 2.00 (d, J=3.8 Hz, 1 H), 5.24 (m, 1 H), 7.19 (d, J=8.6 Hz, 1 H), 7.33 (dd, J=8.6, 2.5 Hz, 1 H), 7.75 (d, J=2.5 Hz, 1 H).

Workup

  1. customquenched with saturated NH4Cl
  2. extractionextracted with EtOAc
  3. washThe organic extracts were washed with 1N HCl, brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated to an oil
  6. customThe oil was purified by flash column chromatography (0% to 10% EtOAc in hexanes)

Sources & evidence

ORD record
ord-7ff39b8330664b8dbdc7e60ecc05b459
Source dataset
uspto-grants-2006_12
Patent number
US07148226B2

Reaction notes

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