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

HRID 84718

反応式

HRID 84718 の反応式
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

参加物

9

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 4

HCID 178418397HCID 178418397、化合物触媒HCID 702Ethanol溶媒HCID 962Water溶媒HCID 1140Toluene溶媒

実験手順

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 precipitate 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.

後処理

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

出典と根拠

ORDレコード
ord-5409c3144e68437aa58ddb286d560201
出典データセット
uspto-grants-2014_09
特許番号
US08846945B2

関連ノート

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