Potassium Carbonate → Tert-butyl-3-(4-tolyl)benzoate

HRID 1018967ノート

反応式

HRID 1018967 の反応式
[CH3:1][C:2]1[CH:7]=[CH:6][C:5](B(O)O)=[CH:4][CH:3]=1.[C:11]([O:15][C:16](=[O:24])[C:17]1[CH:22]=[CH:21][CH:20]=[C:19](I)[CH:18]=1)([CH3:14])([CH3:13])[CH3:12].C([O-])([O-])=O.[K+].[K+]>COCCOC.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>[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:21]2[CH:20]=[CH:19][CH:18]=[C:17]([C:16]([O:15][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:24])[CH:22]=2)=[CH:4][CH:3]=1

参加物

6

反応物 3

HCID 11430Potassium CarbonateHCID 79799Tolylboronic acidHCID 18386959tert-Butyl 3-iodobenzoate

生成物 1

HCID 18398672Tert-butyl-3-(4-tolyl)benzoate収率 78.2%

試薬・触媒・溶媒 2

HCID 178418397HCID 178418397、化合物触媒HCID 80711,2-Dimethoxyethane溶媒

実験手順

A mixture of 4-methylphenylboronic acid (0.65 g, 4.3 mmol), t-butyl-3-iodobenzoate (0.87 g, 2.86 mmol), K2CO3 (0.59 g, 4.3 mmol), and (Ph3P)4 Pd (0.17 g, 0.14 mmol) in DME (15 mL) was degassed and flushed with N2 before being brought to reflux for 2 h. Following a standard aqueous/EtOAc work-up, the residue was triturated with 1:10 EtOAc/hexane. The excess boronic acid was removed by filtration, and the filtrate was concentrated to give an oil which was purified by flash chromatography (hexane) to give an oil (0.6 g). This material (≈60% pure) was used as such for the next step.

後処理

  1. customwas degassed
  2. customflushed with N2
  3. temperatureto reflux for 2 h
  4. customthe residue was triturated with 1:10 EtOAc/hexane
  5. customThe excess boronic acid was removed by filtration
  6. concentrationthe filtrate was concentrated
  7. customto give an oil which
  8. customwas purified by flash chromatography (hexane)

出典と根拠

ORDレコード
ord-8b042612c06344d6a445f3356df15688
出典データセット
uspto-grants-2002_11
特許番号
US06486141B2

反応ノート

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