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Triethylamine → 5'-Methoxycarbonyl-2'-methylbiphenyl-4-carboxylic acid

HRID 399273
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HRID 399273 반응식
Br[C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][C:11]=1[CH3:12])[C:5]([O:7][CH3:8])=[O:6].B([C:16]1[CH:24]=[CH:23][C:19]([C:20]([OH:22])=[O:21])=[CH:18][CH:17]=1)(O)O.C(N(CC)CC)C>CN(C=O)C.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>[CH3:8][O:7][C:5]([C:4]1[CH:9]=[CH:10][C:11]([CH3:12])=[C:2]([C:16]2[CH:24]=[CH:23][C:19]([C:20]([OH:22])=[O:21])=[CH:18][CH:17]=2)[CH:3]=1)=[O:6]
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참가 물질

6

반응물 3

HCID 8471TriethylamineHCID 3121834-Carboxyphenylboronic AcidHCID 7015747Methyl 3-bromo-4-methylbenzoate

생성물 1

HCID 218337565'-Methoxycarbonyl-2'-methylbiphenyl-4-carboxylic acid수율 85%

시약·촉매·용매 2

HCID 178418397HCID 178418397, 화합물촉매
HCID 6228
Dimethylformamide
용매

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온도
100 °C

실험 절차

A stirred solution of methyl 3-bromo-4-methylbenzoate (2.6 g, 0.011 mole) in dry DMF (20 ml) under argon was treated with 4-boronobenzoic acid (1.85 g, 0.011 mole) and tetrakis (triphenylphosphine) palladium (O) (400 mg), followed by triethylamine (4.68 ml, 0.046 mole). The mixture was heated at 100° C. for 18 hours, then concentrated in vacuo. The residue was treated with ethyl acetate and extracted with 10% NaHCO3 solution. The basic extract was acidified with dil. HCl and extracted with ethyl acetate. The extract was dried (Na2SO4) and concentrated in vacuo to afford the title compound as a light orange solid (2.12 g, 85%).

후처리

  1. concentrationconcentrated in vacuo
  2. additionThe residue was treated with ethyl acetate
  3. extractionextracted with 10% NaHCO3 solution
  4. extractionThe basic extract
  5. extractionextracted with ethyl acetate
  6. dry with materialThe extract was dried (Na2SO4)
  7. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-a522e5a7a02241b489658319e3d6f1e9
출처 데이터셋
uspto-grants-1998_10
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05817833

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