Boron Trichloride → 4-Chloro-2,6-dimethoxyphenol

HRID 1891417Notes

Reaction equation

HRID 1891417 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([O:12][CH3:13])[C:5]([O:10]C)=[C:6]([O:8][CH3:9])[CH:7]=1.B(Cl)(Cl)Cl>C(Cl)Cl>[Cl:1][C:2]1[CH:7]=[C:6]([O:8][CH3:9])[C:5]([OH:10])=[C:4]([O:12][CH3:13])[CH:3]=1

Participants

4

Reactant 2

HCID 25135Boron TrichlorideHCID 236178472675-80-1

Product 1

HCID 441546614-Chloro-2,6-dimethoxyphenolYield 98%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution 37a) (4.67 g, 23.1 mmol) in dry DCM (40 mL) at 0° C. under nitrogen was added BCl3 (1M in DCM, 24 mL, 24.0 mmol) drop-wise. The solution was allowed to warm to room temperature over 3.5 h. The reaction was quenched with the addition of H2O (40 mL) and the product extracted with EtOAc (3×30 mL). The organics were pooled, dried over Na2SO4, filtered and concentrated in vacuo. The crude product was purified by flash chromatography (silica gel, EtOAc/Petroleum Spirit, 2:8) to give the title compound as a white solid (4.29 g, 98%). 1H NMR (300 MHz, CDCl3) δ 6.58 (s, 2H), 5.41 (s, 1H), 3.88 (s, 6H), ESIMS m/z [M+H]+ 187.3.

Workup

  1. customThe reaction was quenched with the addition of H2O (40 mL)
  2. extractionthe product extracted with EtOAc (3×30 mL)
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe crude product was purified by flash chromatography (silica gel, EtOAc/Petroleum Spirit, 2:8)

Sources & evidence

ORD record
ord-503d2cb1afc043cd854617131d72ac29
Source dataset
uspto-grants-2013_08
Patent number
US08507539B2

Reaction notes

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