Dichloromethane → Methyl 3-methyl-4'-nitrobiphenyl-4-carboxylate

HRID 403859ノート

反応式

HRID 403859 の反応式
Br[C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[C:4]([CH3:12])[CH:3]=1.CC1(C)C(C)(C)OB([C:21]2[CH:26]=[CH:25][C:24]([N+:27]([O-:29])=[O:28])=[CH:23][CH:22]=2)O1.C(Cl)Cl.C([O-])([O-])=O.[Na+].[Na+]>CN(C=O)C.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].O>[CH3:12][C:4]1[CH:3]=[C:2]([C:21]2[CH:26]=[CH:25][C:24]([N+:27]([O-:29])=[O:28])=[CH:23][CH:22]=2)[CH:11]=[CH:10][C:5]=1[C:6]([O:8][CH3:9])=[O:7]

参加物

8

反応物 4

HCID 6344DichloromethaneHCID 10340Sodium CarbonateHCID 27735554,4,5,5-Tetramethyl-2-(4-nitrophenyl)-1,3,2-dioxaborolaneHCID 22031226Methyl 4-bromo-2-methylbenzoate

生成物 1

HCID 59385226Methyl 3-methyl-4'-nitrobiphenyl-4-carboxylate

試薬・触媒・溶媒 3

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)触媒HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

反応条件

温度
82.5 °C

実験手順

The compound of example 219 (10 g, 0.044 mol), 4,4,5,5-tetramethyl-2-(4-nitrophenyl)-1,3,2-dioxaborolane (13.16 gm, 0.0528 mole) and Pd(dppf)Cl2:CH2Cl2 (1.07 g, 0.00132 mol) were taken in DMF (250 mL) under an argon atmosphere. To this reaction mixture, degassed 2M solution of Na2CO3 (14 g, 0.132 mol, 66.5 mL) was added. The reaction mixture was stirred at 80-85° C. for 1 to 1.5 h. After completion of the reaction, water was added and the product obtained was extracted with ether. The combined ether layer was washed with brine and dried over anhydrous Na2SO4 or MgSO4. The solvent was evaporated and the product was purified by column (silica gel, 20% ethyl acetate in petroleum ether) to obtain the title compound.

後処理

  1. additionwas added
  2. additionwas added
  3. customthe product obtained
  4. extractionwas extracted with ether
  5. washThe combined ether layer was washed with brine
  6. dry with materialdried over anhydrous Na2SO4 or MgSO4
  7. customThe solvent was evaporated
  8. customthe product was purified by column (silica gel, 20% ethyl acetate in petroleum ether)

出典と根拠

ORDレコード
ord-f22d68aecef143089cc2c8ab56492826
出典データセット
uspto-grants-2014_06
特許番号
US08748426B2

反応ノート

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