Potassium Carbonate → Methyl 2'-methyl-2-nitro-1,1'-biphenyl-4-carboxylate

HRID 1950810

반응식

HRID 1950810 반응식
Br[C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][C:3]=1[N+:12]([O-:14])=[O:13].[C:15]1([CH3:24])[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1B(O)O.C(=O)([O-])[O-].[K+].[K+]>C1(C)C=CC=CC=1.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>[CH3:24][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][C:3]=1[N+:12]([O-:14])=[O:13]

참가 물질

7

반응물 3

HCID 11430Potassium CarbonateHCID 27332672-Methylphenyl boronic acidHCID 2736829Methyl 4-bromo-3-nitrobenzoate

생성물 1

HCID 59606541Methyl 2'-methyl-2-nitro-1,1'-biphenyl-4-carboxylate수율 79.9%

시약·촉매·용매 3

HCID 178418397HCID 178418397, 화합물촉매HCID 962Water용매HCID 1140Toluene용매

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온도
120 °C

실험 절차

A suspension of methyl 4-bromo-3-nitrobenzoate (Chess 1687; 3 g; 11.53 mmol; 1 eq.), o-tolylboronic acid (Aldrich 393606; 1.88 g; 13.84 mmol; 1.2 eq.), potassium carbonate (7.97 g, 57.68 mmol, 5 eq.) and tetrakis(triphenylphosphine)palladium(0) (668.2 mg, 0.577 mmol, 0.05 eq.) in toluene (15 mL) and water (15 mL) was stirred at 120° C. for 14 hours. The resulting mixture was allowed to return to room temperature and the two phases were separated. The organic layer was concentrated in vacuo and purified by column chromatography (c-hexane) to afford the title compound (2.5 g, 79%) as a white solid.

후처리

  1. customto return to room temperature
  2. customthe two phases were separated
  3. concentrationThe organic layer was concentrated in vacuo
  4. custompurified by column chromatography (c-hexane)

출처 및 근거

ORD 기록
ord-3d02522246ac447c9e5c88343e4e7d80
출처 데이터셋
uspto-grants-2013_03
특허 번호
US08404676B2

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