HCID 86628018, compound → 8-Bromo-6-chloro-2H-1-benzopyran-2-one

HRID 2233327Notes

Reaction equation

HRID 2233327 reaction equation
[Br:1][C:2]1[C:3]([OH:15])=[C:4](/[CH:9]=[CH:10]/[C:11]([O:13]C)=O)[CH:5]=[C:6]([Cl:8])[CH:7]=1>C1C2C(CCCC2)CCC1>[Br:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[C:4]2[C:3]=1[O:15][C:11](=[O:13])[CH:10]=[CH:9]2

Participants

3

Reactant 1

HCID 86628018HCID 86628018, compound

Product 1

HCID 187215758-Bromo-6-chloro-2H-1-benzopyran-2-oneYield 95%

Reagents, catalysts & solvents 1

HCID 7044DecalinSolvent

Procedure

A solution of methyl (2E)-3-(3-bromo-5-chloro-2-hydroxyphenyl)-2-propenoate (1.45 g; 5.0 mmol) in decalin (5 mL) was heated in a sand bath at 200° C. for 48 h. The reaction was then cooled to RT and hexanes (10 mL) was added. The solid was collected by suction filtration and washed with hexanes. Drying under high vacuum gave the title compound (1.2 g, 95%) as a tan solid: 1H NMR (400 MHz, DMSO-d6) δ 7.78 (s, 1H), 7.63 (d, J=9.6 Hz, 1H)), 7.46 (s, 1H), 6.52 (d, J=9.6 Hz, 1H); MS (ES) m/e 259, 261 (M+H)+.

Workup

  1. filtrationThe solid was collected by suction filtration
  2. washwashed with hexanes
  3. customDrying under high vacuum

Sources & evidence

ORD record
ord-ae449f223cad4c949e91e431095a06b8
Source dataset
uspto-grants-2010_05
Patent number
US07709496B2

Reaction notes

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