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

HRID 1018967노트

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HRID 1018967 반응식
[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

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 178418397HCID 178418397, 화합물촉매HCID 80711,2-Dimethoxyethane용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-8b042612c06344d6a445f3356df15688
출처 데이터셋
uspto-grants-2002_11
특허 번호
US06486141B2

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