Pyridine → 4-Bromo-2-methylphenyl acetate

HRID 400590Notes

Reaction equation

HRID 400590 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[C:4]([CH3:9])[CH:3]=1.N1C=CC=CC=1.[C:16](Cl)(=[O:18])[CH3:17]>ClCCl>[C:16]([O:8][C:5]1[CH:6]=[CH:7][C:2]([Br:1])=[CH:3][C:4]=1[CH3:9])(=[O:18])[CH3:17]

Participants

5

Reactant 3

HCID 1049PyridineHCID 6367Acetyl chlorideHCID 168964-Bromo-2-methylphenol

Product 1

HCID 600267744-Bromo-2-methylphenyl acetateYield 115.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

An ice-cold solution of 4-bromo-2-methylphenol (5.6 g, 30 mmol) and pyridine (6.1 mL, 75 mmol) in 50 mL of anhydrous dichloromethane was treated with a solution of acetyl chloride (2.8 mL, 26 mmol) in 5 mL of anhydrous dichloromethane. After 2 hours, the reaction mixture was concentrated in vacuo. The resulting residue was treated with crushed ice, diluted with 150 mL of dichloromethane, washed with water, dried over sodium sulfate, filtered, and concentrated in vacuo to give 6.9 g of 4-bromo-2-methylphenyl acetate as a light brown oil (quantitative yield).

Workup

  1. concentrationthe reaction mixture was concentrated in vacuo
  2. additionThe resulting residue was treated with crushed ice
  3. additiondiluted with 150 mL of dichloromethane
  4. washwashed with water
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-9f5145793a12429d8e9533aa5913b8f7
Source dataset
uspto-grants-2014_06
Patent number
US08741897B2

Reaction notes

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