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

HRID 1068063
ノート
印刷プレビュー

反応式

HRID 1068063 の反応式
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
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

7

反応物 2

HCID 637114Dimethyl iodoterephthalateHCID 27332672-Methylphenyl boronic acid

生成物 1

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

試薬・触媒・溶媒 4

HCID 11776Triphenylphosphine触媒HCID 167845palladium(II) acetate触媒
HCID 1140
Toluene
溶媒
HCID 10340Sodium Carbonate溶媒

反応条件

温度
77.5 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-8cc77ee3f67847b5895769d7d676e09d
出典データセット
uspto-grants-2001_06
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06248919B1

反応ノート

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