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Hydrogen Bromide → 2-butyl-N-(4'-hydroxy[1,1'-biphenyl]-4-yl)-1-benzofuran-3-carboxamide

HRID 493506
Notes
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Reaction equation

HRID 493506 reaction equation
[CH2:1]([C:5]1[O:6][C:7]2[CH:16]=[CH:15][CH:14]=[CH:13][C:8]=2[C:9]=1[C:10](Cl)=[O:11])[CH2:2][CH2:3][CH3:4].Br.[NH2:18][C:19]1[CH:24]=[CH:23][C:22]([C:25]2[CH:30]=[CH:29][C:28]([OH:31])=[CH:27][CH:26]=2)=[CH:21][CH:20]=1.C(N(CC)CC)C>C1COCC1>[CH2:1]([C:5]1[O:6][C:7]2[CH:16]=[CH:15][CH:14]=[CH:13][C:8]=2[C:9]=1[C:10]([NH:18][C:19]1[CH:20]=[CH:21][C:22]([C:25]2[CH:30]=[CH:29][C:28]([OH:31])=[CH:27][CH:26]=2)=[CH:23][CH:24]=1)=[O:11])[CH2:2][CH2:3][CH3:4]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 260Hydrogen BromideHCID 8471TriethylamineHCID 145654-Amino-4'-hydroxybiphenylHCID 185053462-Butyl-benzofuran-3-carbonyl chloride

Product 1

HCID 688605712-butyl-N-(4'-hydroxy[1,1'-biphenyl]-4-yl)-1-benzofuran-3-carboxamideYield 62.9%

Reagents, catalysts & solvents 1

HCID 8028
Tetrahydrofuran
Solvent
2×

Procedure

2-Butyl-benzofuran-3-carbonyl chloride (2.22 g, 9.36 mmol), prepared in step 2 of Example 4, in 40 mL of anhydrous THF was added under nitrogen dropwise over 20 minutes to a mixture of the HBr salt of 4′-amino-biphenyl-4-ol (3.26 g, 12.3 mmol), prepared in the previous step, and triethylamine (3.42 mL, 24.5 mmol) in 100 mL of anhydrous THF at ice bath temperature. After the addition the reaction was stirred at room temperature for 20 h. The reaction was filtered and the filtrate concentrated under reduced pressure to give a solid. Purification of the solid on 1 Kg of silica gel (230-400 mesh) using 30% ethyl acetate-hexane as the eluent gave 2-butyl-N-(4′-hydroxy[1,1′-biphenyl]-4-yl)-1-benzofuran-3-carboxamide (2.27 g, 48%) as an off-white solid, mp 181-183° C.; MS (APCI) m/z 386 [M+H]+. Elemental Analysis for C25H23NO3: Calc'd: C, 77.90; H, 6.01; N, 3.63; Found: C, 77.48; H, 5.86; N, 3.56.

Workup

  1. additionAfter the addition the reaction
  2. filtrationThe reaction was filtered
  3. concentrationthe filtrate concentrated under reduced pressure
  4. customto give a solid
  5. customPurification of the solid on 1 Kg of silica gel (230-400 mesh)

Sources & evidence

ORD record
ord-3c7bfad7abf04535a7a1935a85ff913d
Source dataset
uspto-grants-2009_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07534894B2

Reaction notes

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