Methanol → (5-Bromo-2,3-dichlorophenyl)methanol

HRID 337583Notes

Reaction equation

HRID 337583 reaction equation
CO.[Br:3][C:4]1[CH:5]=[C:6]([Cl:13])[C:7]([Cl:12])=[C:8]([CH:11]=1)[CH:9]=[O:10].[BH4-].[Na+]>C1COCC1>[Br:3][C:4]1[CH:5]=[C:6]([Cl:13])[C:7]([Cl:12])=[C:8]([CH2:9][OH:10])[CH:11]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 4311764Sodium borohydrideHCID 772312025-Bromo-2,3-dichlorobenzaldehyde

Product 1

HCID 66896066(5-Bromo-2,3-dichlorophenyl)methanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a 5:1 (v/v) MeOH:THF solution (0.38 M) of 5-bromo-2,3-dichlorobenzaldehyde (1 eq.) from Step 1, Amine 5 was added at 0° C. sodium borohydride (1.1 eq.) portionwise over 45 min. The reaction solution was stirred at 0° C. for 2 h before the volatiles were removed in vacuo. The resulting residue was then partitioned between ether and 10% aq. HCl. The aqueous layer was separated and back-extracted with ether. The combined organic extracts were washed further with 1 N aq. NaOH, water and brine, dried Na2SO4, filtered and the filtrate concentrated in vacuo. Purification of the crude product thus obtained by way of flash chromatography (SiO2, 9:1 (v/v) Hex:EtOAc→3:7 (v/v) Hex:EtOAc) afforded the title compound as a white solid.

Workup

  1. customwere removed in vacuo
  2. customThe resulting residue was then partitioned between ether and 10% aq. HCl
  3. customThe aqueous layer was separated
  4. extractionback-extracted with ether
  5. washThe combined organic extracts were washed further with 1 N aq. NaOH, water and brine, dried Na2SO4
  6. filtrationfiltered
  7. concentrationthe filtrate concentrated in vacuo
  8. customPurification of the crude product
  9. customthus obtained by way of flash chromatography (SiO2, 9:1 (v/v) Hex:EtOAc→3:7 (v/v) Hex:EtOAc)

Sources & evidence

ORD record
ord-f3f42687c21b4a409166931e6db466ee
Source dataset
uspto-grants-2014_11
Patent number
US08889714B2

Reaction notes

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