Bromine → HCID 86587386, compound

HRID 1357255Notes

Reaction equation

HRID 1357255 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][N:15]([CH3:29])[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][CH3:28])=[O:17])[CH:8]=[CH:7]2>C(O)(=O)C>[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][N:15]([CH3:29])[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][CH3:28])=[O:17])=[CH:10]2

Participants

4

Reactant 2

HCID 24408BromineHCID 865873852-Ethyl-benzofuran-3-carboxylic acid (6-hydroxy-naphthalen-2-ylmethyl)-methyl-amide

Product 1

HCID 86587386HCID 86587386, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

A solution of bromine in 50 mL glacial acetic acid was added dropwise under nitrogen over 3 h to a solution of 2-ethyl-benzofuran-3-carboxylic acid (6-hydroxy-naphthalen-2-ylmethyl)-methyl-amide (1.5 g, 4.17 mmol), prepared in the previous step, in 150 mL glacial acetic acid at room temperature. The reaction stirred for 17 h (overnight). The solvent was removed under reduced pressure. The residue was dissolved in methylene chloride, extracted with 5% sodium bicarbonate, dried (MgSO4) and solvent removed under reduced pressure to give 2-ethyl-benzofuran-3-carboxylic acid (5-bromo-6-hydroxy-naphthalen-2-ylmethyl)-methyl-amide (1.74 g, 95%) as a brown solid, mp 176-178° C.

Workup

  1. customThe solvent was removed under reduced pressure
  2. dissolutionThe residue was dissolved in methylene chloride
  3. extractionextracted with 5% sodium bicarbonate
  4. dry with materialdried (MgSO4) and solvent
  5. customremoved under reduced pressure

Sources & evidence

ORD record
ord-cad9c1354acc4fb68c0b111905d665c0
Source dataset
uspto-grants-2003_07
Patent number
US06589970B2

Reaction notes

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