Acetic Acid Mixture with Hydrobromic Acid → HCID 22994353, compound

HRID 1167820Notes

Reaction equation

HRID 1167820 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:9](=[O:31])[O:10][C:11]3[C:16]([C:17]=2[CH2:18][C:19]2[CH:24]=[CH:23][C:22]([O:25][CH2:26][CH2:27][Br:28])=[CH:21][CH:20]=2)=[CH:15][CH:14]=[C:13]([O:29]C)[CH:12]=3)=[CH:4][CH:3]=1.Br.CC(O)=O>O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[C:9](=[O:31])[O:10][C:11]3[C:16]([C:17]=2[CH2:18][C:19]2[CH:24]=[CH:23][C:22]([O:25][CH2:26][CH2:27][Br:28])=[CH:21][CH:20]=2)=[CH:15][CH:14]=[C:13]([OH:29])[CH:12]=3)=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 21893785Acetic Acid Mixture with Hydrobromic AcidHCID 22994352HCID 22994352, compound

Product 1

HCID 22994353HCID 22994353, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 3-(4-chlorophenyl)-4-(4-(2-bromoethoxy)benzyl)-7-methoxychromen-2-one (16.5 grams, 33 mmol) and 150 mL of 30% HBr/HOAc in a sealed tube was warmed at 100° C. for 8 h. The reaction mixture was cooled to room temperature and poured into 300 mL of water. The resulting solid was collected by filtration and purified using flash chromatography to provide the desired product (12.5 g, 78%). 1H NMR (300 MHz, DMSO) δ 10.55 (s, 1H), 7.47 (d, 2H, J=8.5 Hz), 7.43 (d, 1H, J=8.8 Hz), 7.33 (d, 2H, J=8.5 Hz), 7.05 (d, 2H, J=8.5 Hz), 6.83 (d, 2H, J=8.5 Hz), 6.75 (d, 1H, J=2.2 Hz), 6.70 (dd, 1H, J=8.8, 2.2 Hz), 4.24 (t, 2H, J=5.7 Hz), 3.94 (s, 2H), 3.76 (t, 2H, J=5.7 Hz). MS (ESI) m/z 486 (M+H)+.

Workup

  1. filtrationThe resulting solid was collected by filtration
  2. custompurified

Sources & evidence

ORD record
ord-009504e228ab42e1b41fef2c134f659c
Source dataset
uspto-grants-2003_09
Patent number
US06620838B1

Reaction notes

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