Acetyl chloride → 6-Bromo-7-acetoxy-4-methylcoumarin

HRID 993358Notes

Reaction equation

HRID 993358 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[OH:12])[O:8][C:7](=[O:13])[CH:6]=[C:5]2[CH3:14].C(N(CC)CC)C.[C:22](Cl)(=[O:24])[CH3:23]>C(#N)C>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[O:12][C:22](=[O:24])[CH3:23])[O:8][C:7](=[O:13])[CH:6]=[C:5]2[CH3:14]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 184103436-Bromo-7-hydroxy-4-methyl-2H-1-benzopyran-2-one

Product 1

HCID 184103326-Bromo-7-acetoxy-4-methylcoumarinYield 76.7%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 453.1 mg (1.776 mmol) of compound 17 and 545 mL (3.9 mmol) of triethylamine in dry acetonitrile (5 mL) was added 255 mL (3.59 mmol) of acetyl chloride. The reaction mixture was stirred for 15 hours at room temperature, quenched with 1N HCl, diluted with chloroform and separated. The organic layer was washed with saturated aqueous NaHCO3 and saturated aqueous brine, dried (MgSO4) and evaporated to dryness to yield 404.9 mg (1.363 mmol, 76.7% yield) of the crude compound 18. This compound was used for the next reaction without a further purification.

Workup

  1. customquenched with 1N HCl
  2. additiondiluted with chloroform
  3. customseparated
  4. washThe organic layer was washed with saturated aqueous NaHCO3 and saturated aqueous brine
  5. dry with materialdried (MgSO4)
  6. customevaporated to dryness

Sources & evidence

ORD record
ord-018a98b0825242c18b2257ce703a50eb
Source dataset
uspto-grants-2002_10
Patent number
US06472541B2

Reaction notes

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