Cesium carbonate → 4'-Methyl-5-nitro-[1,1'-biphenyl]-3-carboxylic acid

HRID 1642290Notes

Reaction equation

HRID 1642290 reaction equation
I[C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([N+:11]([O-:13])=[O:12])[CH:10]=1)[C:5]([OH:7])=[O:6].B(O)(O)[C:15]1[CH:16]=[CH:17][C:18]([CH3:21])=[CH:19][CH:20]=1.C([O-])([O-])=O.[Cs+].[Cs+].[OH-].[Na+]>C1(C)C=CC=CC=1.C(O)C.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>[CH3:21][C:18]1[CH:19]=[CH:20][C:15]([C:2]2[CH:10]=[C:9]([N+:11]([O-:13])=[O:12])[CH:8]=[C:4]([C:5]([OH:7])=[O:6])[CH:3]=2)=[CH:16][CH:17]=1

Participants

9

Reactant 4

HCID 10796Cesium carbonateHCID 14798Sodium HydroxideHCID 79799Tolylboronic acidHCID 805803-Iodo-5-nitrobenzoic acid

Product 1

HCID 532248984'-Methyl-5-nitro-[1,1'-biphenyl]-3-carboxylic acidYield 97.2%

Reagents, catalysts & solvents 4

HCID 178418397HCID 178418397, compoundCatalystHCID 702EthanolSolventHCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

To a stirred solution of 3-iodo-5-nitrobenzoic acid (15.48 g, 52.83 mmol) and Pd(Ph3P)4 (1.84 g, 1.69 mmol) in 300 ml of toluene and 50 ml of ethanol was added p-tolylboronic acid (7.87 g, 58.11 mmol) and a solution of Cs2CO3 (18.89 g, 58.11 mmol) in 20 ml water at room temperature. The reaction was brought to reflux for 18 hours and then cooled to room temperature. To the solution was added 2N NaOH, and the reaction mixture was stirred for 30 minutes. The organic phase was separated, and the aqueous phase was adjusted to PH<4 using 12N HCl. The resulting solid preciptate was filtered and washed with toluene to afford 13.2 g of 4′-methyl-5-nitro-biphenyl-3-carboxylic acid as light yellow solid (97.2%). MS (M+H)=258.

Workup

  1. customat room temperature
  2. temperatureto reflux for 18 hours
  3. customThe organic phase was separated
  4. filtrationThe resulting solid preciptate was filtered
  5. washwashed with toluene

Sources & evidence

ORD record
ord-0be6303cda8a4c5eadf6adfcd22710b0
Source dataset
uspto-grants-2012_02
Patent number
US08119644B2

Reaction notes

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