Bromine → HCID 91144016, compound

HRID 1357235Notes

Reaction equation

HRID 1357235 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[CH3:27])=[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[CH3:27])=[O:17])=[CH:10]2

Participants

4

Reactant 2

HCID 24408BromineHCID 90718122HCID 90718122, compound

Product 1

HCID 91144016HCID 91144016, compoundYield 104.5%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

Bromine (83 μL, 1.61 mmol) in 15 mL of glacial HOAc was added under nitrogen dropwise over 3 h to a solution of 2-methyl-benzofuran-3-carboxylic acid (6-hydroxy-naphthalen-2-ylmethyl)-amide (537 mg, 1.62 mmol), prepared in the previous step, in 60 mL of glacial HOAc at room temperature. After the addition the reaction was stirred at room temperature for 1 h. The solvent was removed under reduced pressure and the residue partitioned between 20% MeOH in methylene chloride and 5% NaHCO3. After separating the organic layer the aqueous layer was extracted three times with 20% MeOH in methylene chloride. The combined extracts were dried (MgSO4) and the solvent removed under reduced pressure to give 2-methyl-benzofuran-3-carboxylic acid (5-bromo-6-hydroxy-naphthalen-2-ylmethyl)-amide (690 mg, 100%) as a brown solid, mp 179-181° C.

Workup

  1. additionAfter the addition the reaction
  2. customThe solvent was removed under reduced pressure
  3. customthe residue partitioned between 20% MeOH in methylene chloride and 5% NaHCO3
  4. customAfter separating the organic layer the aqueous layer
  5. extractionwas extracted three times with 20% MeOH in methylene chloride
  6. dry with materialThe combined extracts were dried (MgSO4)
  7. customthe solvent removed under reduced pressure

Sources & evidence

ORD record
ord-497cf2b63bb44be8b3c474bdfad90f5b
Source dataset
uspto-grants-2003_07
Patent number
US06589970B2

Reaction notes

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