Water → HCID 68859917, compound

HRID 493497Notes

Reaction equation

HRID 493497 reaction equation
B(Br)(Br)Br.[CH2:5]([N:12]([CH2:28][C:29]1[CH:34]=[CH:33][C:32]([C:35]2[CH:40]=[CH:39][C:38]([O:41]C)=[C:37]([Br:43])[CH:36]=2)=[CH:31][CH:30]=1)[C:13]([C:15]1[C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=2[O:17][C:16]=1[CH2:24][CH2:25][CH2:26][CH3:27])=[O:14])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.C(=O)=O.CC(C)=O.O>C(Cl)Cl>[CH2:5]([N:12]([CH2:28][C:29]1[CH:30]=[CH:31][C:32]([C:35]2[CH:40]=[CH:39][C:38]([OH:41])=[C:37]([Br:43])[CH:36]=2)=[CH:33][CH:34]=1)[C:13]([C:15]1[C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=2[O:17][C:16]=1[CH2:24][CH2:25][CH2:26][CH3:27])=[O:14])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 25134Boron tribromideHCID 18522661Acetone cardice2×HCID 68860657HCID 68860657, compound

Product 1

HCID 68859917HCID 68859917, compoundYield 75.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Boron tribromide (22.0 mL of a 1 M solution in methylene chloride; 22.0 mmol) was added under nitrogen dropwise over 30 minutes to a solution N-benzyl-N-[(3′-bromo-4′-methoxy-1,1′-biphenyl-4-yl)methyl]-2-butyl-1-benzofuran-3-carboxamide (4.2 g, 7.22 mmol), of 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 3 h. At ice bath temperature water (100 mL) was added dropwise. The aqueous layer was separated and extracted two times with methylene chloride. The extracts were combined, extracted with saturated NaCl, dried (MgSO4) and the solvent removed under reduced pressure to give N-benzyl-N-[(3′-bromo-4′-hydroxy-1,1′-biphenyl-4-yl)methyl]-2-butyl-1-benzofuran-3-carboxamide (3.1 g, 72%) as an off-white solid, MS (ESI) m/z 568 [M+H]+. Elemental Analysis for C33H30BrNO3: Calc'd: C, 69.72; H, 5.32; N, 2.46; Found: C, 68.69; H, 5.42; N, 2.28.

Workup

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

Sources & evidence

ORD record
ord-249b0f235bd24b6790eaf7a1740b6952
Source dataset
uspto-grants-2009_05
Patent number
US07534894B2

Reaction notes

Loading…