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Dimethyl iodoterephthalate → Dimethyl 2'-methyl(1,1'-biphenyl)-2.5-dicarboxylate

HRID 1068063
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HRID 1068063 반응식
I[C:2]1[CH:11]=[C:10]([C:12]([O:14][CH3:15])=[O:13])[CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].[C:16]1([CH3:25])[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1B(O)O>C1(C)C=CC=CC=1.C([O-])([O-])=O.[Na+].[Na+].C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[CH3:25][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[C:2]1[C:3]([C:4]([O:6][CH3:7])=[O:5])=[CH:8][CH:9]=[C:10]([C:12]([O:14][CH3:15])=[O:13])[CH:11]=1
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 2

HCID 637114Dimethyl iodoterephthalateHCID 27332672-Methylphenyl boronic acid

생성물 1

HCID 11277578Dimethyl 2'-methyl(1,1'-biphenyl)-2.5-dicarboxylate수율 99%

시약·촉매·용매 4

HCID 11776Triphenylphosphine촉매HCID 167845palladium(II) acetate촉매
HCID 1140
Toluene
용매
HCID 10340Sodium Carbonate용매

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온도
77.5 °C

실험 절차

A mixture of dimethyl iodoterephthalate (2.41 kg, 7.53 mol), ortho-tolylboronic acid (1.23 kg, 9.04 mol), palladium(II) acetate (16.9 g, 0.08 mol), and triphenylphosphine (79.0 g, 0.30 mol) in deoxygenated toluene (19 L) and 2M Na2CO3 (19 L) was vigorously mechanically stirred for 4 hours at 75-80° C. and cooled to room temperature to provide two distinct layers. The layers were separated, and the organic layer was filtered through a pad of silica gel 60 (4.79 kg of silica gel slurried with 2×10 L of MTBE) with a 40 L MTBE rinse, concentrated to 40 L, stored at 2-8° C. for 18 hours, filtered through a pad of diatomaceous earth (4.91 kg of Celite® 521 slurried in 20 L of MTBE) with a 40 L MTBE rinse to provide a solution of 2.12 kg (99%) of the desired product in MTBE.

후처리

  1. temperaturecooled to room temperature
  2. customto provide two distinct layers
  3. customThe layers were separated
  4. filtrationthe organic layer was filtered through a pad of silica gel 60 (4.79 kg of silica gel slurried with 2×10 L of MTBE) with a 40 L MTBE
  5. washrinse
  6. concentrationconcentrated to 40 L
  7. waitstored at 2-8° C. for 18 hours
  8. filtrationfiltered through a pad of diatomaceous earth (4.91 kg of Celite® 521 slurried in 20 L of MTBE) with a 40 L MTBE
  9. washrinse

출처 및 근거

ORD 기록
ord-8cc77ee3f67847b5895769d7d676e09d
출처 데이터셋
uspto-grants-2001_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06248919B1

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