Bromine → HCID 86587378, compound

HRID 1357232Notes

Reaction equation

HRID 1357232 reaction equation
[Br:1]Br.[OH:3][C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[CH:10]=[C:9]([CH2:14][NH:15][C:16]([C:18]1[C:22]3[CH:23]=[CH:24][CH:25]=[CH:26][C:21]=3[O:20][C:19]=1[CH2:27][CH2:28][CH2:29][CH3:30])=[O:17])[CH:8]=[CH:7]2>CC(O)=O>[Br:1][C:5]1[C:4]([OH:3])=[CH:13][CH:12]=[C:11]2[C:6]=1[CH:7]=[CH:8][C:9]([CH2:14][NH:15][C:16]([C:18]1[C:22]3[CH:23]=[CH:24][CH:25]=[CH:26][C:21]=3[O:20][C:19]=1[CH2:27][CH2:28][CH2:29][CH3:30])=[O:17])=[CH:10]2

Participants

4

Reactant 2

HCID 24408BromineHCID 90735774HCID 90735774, compound

Product 1

HCID 86587378HCID 86587378, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

Bromine (210 μL, 4.02 mmol) in 50 mL of glacial HOAc was added under nitrogen dropwise over 2 h to a solution of 2-butyl-benzofuran-3-carboxylic acid (6-hydroxy-naphthalen-2-ylmethyl)-amide (1.5 g, 4.02 mmol), prepared in step 2 of Example 8, in 300 mL of glacial HOAc at room temperature. After the addition the reaction was stirred at room temperature for 20 h (overnight). The solid formed was collected by filtration and dried under reduced pressure to give 2-butyl-benzofuran-3-carboxylic acid (5-bromo-6-hydroxy-naphthalen-2-ylmethyl)-amide (1.41 g, 81%) as a light gray solid, mp 192-193° C.

Workup

  1. additionAfter the addition the reaction
  2. customThe solid formed
  3. filtrationwas collected by filtration
  4. customdried under reduced pressure

Sources & evidence

ORD record
ord-2314e520fcf3402886fd2f08d96cf93e
Source dataset
uspto-grants-2003_07
Patent number
US06589970B2

Reaction notes

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