Methanol → 2-Chloro-5-nitrophenol

HRID 474224Notes

Reaction equation

HRID 474224 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][C:3]=1[O:11]C.B(Br)(Br)Br.CO.[OH-].[Na+]>ClCCl.O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][C:3]=1[OH:11]

Participants

7

Reactant 4

HCID 887MethanolHCID 14798Sodium HydroxideHCID 25134Boron tribromideHCID 705192-Chloro-5-nitroanisole

Product 1

HCID 692642-Chloro-5-nitrophenolYield 68%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Conditions

Temperature
-20 °C

Procedure

To a stirred solution of 1-chloro-2-methoxy-4-nitrobenzene (20 g, 106.6 mmol) in dichloromethane (500 mL) at −78° C. under a flow of Nitrogen gas, a solution of BBr3 (747 mmol) in dichloromethane was added dropwise. The reaction was stirred overnight at −20° C., then for 1 h at 4° C. To the reaction, 10 mL of MeOH and 100 mL of water were added dropwise. The resulting mixture was made basic with 10% NaOH solution. The aqueous layer was then made acidic and was extracted with chloroform. The combined organic layers were dried with Na2SO4, filtered and concentrated in vacuo to afford the yellow solid 2-chloro-5-nitrophenol (12.5 g, 68%).

Workup

  1. waitfor 1 h at 4° C
  2. additionwere added dropwise
  3. extractionmade acidic and was extracted with chloroform
  4. dry with materialThe combined organic layers were dried with Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-1a1024091b094f568c46dff3481738fc
Source dataset
uspto-grants-2014_01
Patent number
US08637523B2

Reaction notes

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