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Dimethylformamide → Methyl 2'-fluoro-5'-(methyloxy)-2-nitro-1,1'-biphenyl-4-carboxylate

HRID 404342
Notes
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Reaction equation

HRID 404342 reaction equation
Cl[C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][C:3]=1[N+:12]([O-:14])=[O:13].CN(C=O)C.[F:20][C:21]1[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[CH:23][C:22]=1B(O)O.C(=O)([O-])[O-].[K+].[K+]>[Cl-].[Na+].O.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>[F:20][C:21]1[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[CH:23][C:22]=1[C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][C:3]=1[N+:12]([O-:14])=[O:13]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 735797Methyl 4-chloro-3-nitrobenzoateHCID 41572112-Fluoro-5-methoxyphenylboronic acid

Product 1

HCID 57706335Methyl 2'-fluoro-5'-(methyloxy)-2-nitro-1,1'-biphenyl-4-carboxylateYield 99%

Reagents, catalysts & solvents 2

HCID 178418397
HCID 178418397, compound
Catalyst
HCID 57417360Sodium chloride; waterSolvent

Conditions

Temperature
90 °C

Procedure

To a stirred solution of methyl 4-chloro-3-nitrobenzoate (10.00 g, 46 mmol, commercially available from TCI) in DMF (15.00 mL, 194 mmol) at 23° C. was added 2-fluoro-5-methoxyphenylboronic acid (12 g, 70 mmol) (commercially available from Sigma-Aldrich, St. Louis, Mo., USA), potassium carbonate (19 g, 139 mmol), and then tetrakis(triphenylphosphine)palladium (2.1 g, 1.9 mmol). The mixture was heated at 90° C. for 18 hours and then cooled to room temperature. The reaction was diluted with brine and extracted three times with EtOAc. The organic layers were combined, dried over anhydrous MgSO4, and filtered. The organic solvent was removed under reduced pressure and the residue was purified on silica gel (0-40% EtOAc in hexanes) to yield T12.3 as a colorless oil (14.00 g, 99% yield).

Workup

  1. temperaturecooled to room temperature
  2. extractionextracted three times with EtOAc
  3. dry with materialdried over anhydrous MgSO4
  4. filtrationfiltered
  5. customThe organic solvent was removed under reduced pressure
  6. customthe residue was purified on silica gel (0-40% EtOAc in hexanes)

Sources & evidence

ORD record
ord-0e3180df4ea746a5a105839c707d01c2
Source dataset
uspto-grants-2014_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08748462B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes