Methanol → 4-Chloro-2-ethylphenol

HRID 2359282Notes

Reaction equation

HRID 2359282 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([O:8]C)=[C:4]([CH2:10][CH3:11])[CH:3]=1.B(Br)(Br)Br.CO>ClCCl>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[C:4]([CH2:10][CH3:11])[CH:3]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 25134Boron tribromide2×HCID 20592656HCID 20592656, compound

Product 1

HCID 293574-Chloro-2-ethylphenolYield 58%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 4-chloro-2-ethyl-1-methoxybenzene (Preparation 5, 7.0 g, 41.0 mmol) in dichloromethane (20 mL) at 0° C. was added a 1M solution of boron tribromide in dichloromethane (20.5 mL, 20.5 mmol). After 2 hours, further boron tribromide solution (20 mL, 20.0 mmol) was added. After a further 2 hours, methanol was added and the reaction mixture concentrated in vacuo. The residue was purified by silica gel column chromatography (5%-40% ethyl acetate in heptane) to afford the title compound (3.7 g, 58%).

Workup

  1. waitAfter a further 2 hours
  2. concentrationthe reaction mixture concentrated in vacuo
  3. customThe residue was purified by silica gel column chromatography (5%-40% ethyl acetate in heptane)

Sources & evidence

ORD record
ord-58281d64f4a04bc3b606088beb50c667
Source dataset
uspto-grants-2014_04
Patent number
US08685977B2

Reaction notes

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