Boron tribromide → N-[2-(3,4-Dihydroxyphenyl)-3-hydroxy-4-oxo-4H-chromen-6-yl]acetamide

HRID 2301355Notes

Reaction equation

HRID 2301355 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([C:10]3[O:11][C:12]4[C:17]([C:18](=[O:21])[C:19]=3[OH:20])=[CH:16][C:15]([NH:22][C:23](=[O:25])[CH3:24])=[CH:14][CH:13]=4)=[CH:9][C:4]=2[O:3]C1.B(Br)(Br)Br>C(Cl)Cl>[OH:3][C:4]1[CH:9]=[C:8]([C:10]2[O:11][C:12]3[C:17]([C:18](=[O:21])[C:19]=2[OH:20])=[CH:16][C:15]([NH:22][C:23](=[O:25])[CH3:24])=[CH:14][CH:13]=3)[CH:7]=[CH:6][C:5]=1[OH:1]

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 99497772-(benzo[1,3]dioxol-5-yl)-3-hydroxy-6-acetamido-4H-1-benzopyran-4-one

Product 1

HCID 18372820N-[2-(3,4-Dihydroxyphenyl)-3-hydroxy-4-oxo-4H-chromen-6-yl]acetamideYield 93,215,920%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

20 mg (59pmol) of the compound obtained in Example 23 was dissolved in 2 ml of methylenechloride, and the mixture was reacted with excess amount of boron tribromide (BBr3) at room temperature for 3 hours. The resulting product was concentrated. Then the produced solid was washed with methylenechloride and 10% methanol/methylenechloride, filtered, and dried to give 18 mg of the title compound in a yield of 93%.

Workup

  1. concentrationThe resulting product was concentrated
  2. washThen the produced solid was washed with methylenechloride and 10% methanol/methylenechloride
  3. filtrationfiltered
  4. customdried

Sources & evidence

ORD record
ord-4b829a229d4f4b51a90c809765c10599
Source dataset
uspto-grants-2002_12
Patent number
US06500846B1

Reaction notes

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