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Toluene → 3'-Methoxybiphenyl-3-carboxylic acid amide

HRID 347668
Notes
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Reaction equation

HRID 347668 reaction equation
Br[C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5]([NH2:7])=[O:6].C1(C)C=CC=CC=1.C([O-])([O-])=O.[Na+].[Na+].[CH3:24][O:25][C:26]1[CH:27]=[C:28](B(O)O)[CH:29]=[CH:30][CH:31]=1>O.CCO.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:24][O:25][C:26]1[CH:31]=[C:30]([C:2]2[CH:10]=[CH:9][CH:8]=[C:4]([C:5]([NH2:7])=[O:6])[CH:3]=2)[CH:29]=[CH:28][CH:27]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 4

HCID 1140TolueneHCID 10340Sodium CarbonateHCID 898073-BromobenzamideHCID 2734370(3-Methoxyphenyl)boronic acid

Product 1

HCID 671227163'-Methoxybiphenyl-3-carboxylic acid amideYield 74.1%

Reagents, catalysts & solvents 3

HCID 178418397
HCID 178418397, compound
Catalyst
HCID 702EthanolSolvent
HCID 962WaterSolvent

Procedure

To a stirred mixture 3-bromobenzoic acid amide (0.76 g; 3.8 mmol) and toluene (25 mL), Pd(PPh3)4 (0.180 g; 0.16 mmol), a solution of Na2CO3 (2.543 g; 24 mmol) in H2O (10 mL), and one of 3-methoxyphenylboronic acid (1.132 g; 7.45 mmol) in EtOH (10 mL) were added. The mixture was refluxed for 1 h under vigorous stirring, cooled, and the acqueous phase extracted with AcOEt. The combined organic layers were dried over Na2SO4 and concentrated. Purification of the residue by column chromatography (cyclohexane/EtOAc 1:1 then 4:6) and recrystallization gave the desired product (0.64 g) as white solid. Yield 74%. Mp: 138–40° C. (EtOH). MS (EI): m/z 227 (M+, 100%). 1H NMR (CDCl3): δ 3.88 (s, 3H); 5.71 (br s, 1H); 6.11 (br s, 1H); 6.94 (m, 1H); 7.18 (m, 2H); 7.39 (t, 1H); 7.53 (t, 1H); 7.77 (m, 2H); 8.05 (t, 1H) ppm. IR (Nujol): 3327, 3148, 1676, 1640, 1613, 1584 cm−1.

Workup

  1. temperatureThe mixture was refluxed for 1 h under vigorous stirring
  2. temperaturecooled
  3. extractionthe acqueous phase extracted with AcOEt
  4. dry with materialThe combined organic layers were dried over Na2SO4
  5. concentrationconcentrated
  6. customPurification of the residue by column chromatography (cyclohexane/EtOAc 1:1
  7. custom4:6) and recrystallization

Sources & evidence

ORD record
ord-ed744bcc679f47c18f6717b83fd60aaf
Source dataset
uspto-grants-2007_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07176201B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes