Water → HCID 68861339, compound

HRID 493481Notes

Reaction equation

HRID 493481 reaction equation
B(Br)(Br)Br.[Br:5][C:6]1[CH:7]=[C:8]([C:14]2[CH:19]=[CH:18][C:17]([CH2:20][N:21]([CH3:37])[C:22]([C:24]3[C:28]4[CH:29]=[CH:30][CH:31]=[CH:32][C:27]=4[O:26][C:25]=3[CH2:33][CH2:34][CH2:35][CH3:36])=[O:23])=[CH:16][CH:15]=2)[CH:9]=[CH:10][C:11]=1[O:12]C.C(=O)=O.CC(C)=O.O>C(Cl)Cl>[Br:5][C:6]1[CH:7]=[C:8]([C:14]2[CH:15]=[CH:16][C:17]([CH2:20][N:21]([CH3:37])[C:22]([C:24]3[C:28]4[CH:29]=[CH:30][CH:31]=[CH:32][C:27]=4[O:26][C:25]=3[CH2:33][CH2:34][CH2:35][CH3:36])=[O:23])=[CH:18][CH:19]=2)[CH:9]=[CH:10][C:11]=1[OH:12]

Participants

6

Reactant 4

HCID 962WaterHCID 25134Boron tribromideHCID 18522661Acetone cardice2×HCID 68860811HCID 68860811, compound

Product 1

HCID 68861339HCID 68861339, compoundYield 100.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Boron tribromide (31.8 mL of a 1 M solution in methylene chloride; 31.8 mmol) was added under nitrogen dropwise over 30 minutes to a solution of N-[(3′-bromo-4′-methoxy-1,1′-biphenyl-4-yl)methyl]-2-butyl-N-methyl-1-benzofuran-3-carboxamide (5.37 g, 10.6 mmol), prepared in the previous step, in 150 mL of methylene chloride at dry ice-acetone temperature. After the addition the dry ice-acetone bath was replaced with an ice bath and the stirring continued for 1.5 h. At ice bath temperature-water was added dropwise. The aqueous layer was separated and extracted two times with methylene chloride. The extracts were combined, dried (MgSO4) and the solvent removed under reduced pressure to give N-[(3′-bromo-4′-hydroxy-1,1′-biphenyl-4-yl)methyl]-2-butyl-N-methyl-1-benzofuran-3-carboxamide (5.26 g, 100%) as a light brown foam, MS (ESI) m/z 492 [M+H]+. Elemental Analysis for C27H26BrNO3. Calc'd: C, 65.86; H, 5.32; N, 2.84. Found: C, 64.98; H, 5.15; N, 2.63.

Workup

  1. customwas replaced with an ice bath
  2. customThe aqueous layer was separated
  3. extractionextracted two times with methylene chloride
  4. dry with materialdried (MgSO4)
  5. customthe solvent removed under reduced pressure

Sources & evidence

ORD record
ord-d526d35240694c42b60db65cfa6ba799
Source dataset
uspto-grants-2009_05
Patent number
US07534894B2

Reaction notes

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