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

HRID 77740

반응식

HRID 77740 반응식
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

참가 물질

9

반응물 4

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

생성물 1

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

시약·촉매·용매 4

HCID 178418397HCID 178418397, 화합물촉매HCID 702Ethanol용매HCID 962Water용매HCID 1140Toluene용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-5becd28fde534415a762bc73ab40f7db
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08841336B2

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