Bromine → HCID 86587384, compound

HRID 1357250Notes

Reaction equation

HRID 1357250 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]([CH3:31])[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>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]([CH3:31])[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 86587388HCID 86587388, compound

Product 1

HCID 86587384HCID 86587384, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

A solution of bromine in 40 mL glacial acetic acid was added dropwise under nitrogen over 2.5 h to a solution of 2-butyl-benzofuran-3-carboxylic acid (6-hydroxy-naphthalen-2-ylmethyl)-methyl-amide (0.5364 g, 1.358 mmol), prepared in the previous step, in 60 mL of glacial acetic acid. The reaction stirred for 20 h (overnight). The solvent was removed under reduced pressure. The residue was diluted with methylene chloride, extracted with 5% NaHCO3, dried (MgSO4) and the solvent removed under reduced pressure to give 2-butyl-benzofuran-3-carboxylic acid (5-bromo-6-hydroxy-naphthalen-2-ylmethyl)-methyl-amide (0.6981 g, 100%.) as a light yellow foam, MS m/z: 466 [M+H]+.

Workup

  1. customThe solvent was removed under reduced pressure
  2. additionThe residue was diluted with methylene chloride
  3. extractionextracted with 5% NaHCO3
  4. dry with materialdried (MgSO4)
  5. customthe solvent removed under reduced pressure

Sources & evidence

ORD record
ord-2bf63098dde14cc2848c65ec93b167bb
Source dataset
uspto-grants-2003_07
Patent number
US06589970B2

Reaction notes

Loading…