Sodium Carbonate → 2-(2-Formyl-biphenyl-4-yloxy)4-trifluoromethyl-benzonitrile

HRID 1178472ノート

反応式

HRID 1178472 の反応式
Br[C:2]1[CH:20]=[CH:19][C:5]([O:6][C:7]2[CH:14]=[C:13]([C:15]([F:18])([F:17])[F:16])[CH:12]=[CH:11][C:8]=2[C:9]#[N:10])=[CH:4][C:3]=1[CH:21]=[O:22].[C:23]1(B(O)O)[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.C(=O)([O-])[O-].[Na+].[Na+]>C(COC)OC.O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[CH:21]([C:3]1[CH:4]=[C:5]([O:6][C:7]2[CH:14]=[C:13]([C:15]([F:18])([F:17])[F:16])[CH:12]=[CH:11][C:8]=2[C:9]#[N:10])[CH:19]=[CH:20][C:2]=1[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)=[O:22]

参加物

7

反応物 3

HCID 10340Sodium CarbonateHCID 66827Phenylboronic AcidHCID 219303662-(4-Bromo-3-formyl-phenoxy)-4-trifluoromethyl-benzonitrile

生成物 1

HCID 219303872-(2-Formyl-biphenyl-4-yloxy)4-trifluoromethyl-benzonitrile収率 99%

試薬・触媒・溶媒 3

HCID 11776Triphenylphosphine触媒HCID 962Water溶媒HCID 80711,2-Dimethoxyethane溶媒

実験手順

To a mixture of 2-(4-bromo-3-formyl-phenoxy)-4-trifluoromethyl-benzonitrile (1.76 g, 4.76 mmol) and Pd(dba)3 (21.8 mg, 5 mole %) in dimethoxyethane (15 ml) was added a solution of phenylboronic acid (609 mg, 5 mmol), triphenylphosphine (15 mg, 12 mole %) and sodium carbonate (530 mg, 5 mmol) in water (10 ml). The mixture was refluxed for 3 h. The solvent was evaporated off and the aqueous layer was extracted with dichloromethane. The extracts were dried with MgSO4 and filtered through silica. Evaporation yielded a brown solid (1.73 g, 99%).

後処理

  1. temperatureThe mixture was refluxed for 3 h
  2. customThe solvent was evaporated off
  3. extractionthe aqueous layer was extracted with dichloromethane
  4. dry with materialThe extracts were dried with MgSO4
  5. filtrationfiltered through silica
  6. customEvaporation

出典と根拠

ORDレコード
ord-f4f4e5cd517849939e86d6783a9a570a
出典データセット
uspto-grants-2007_10
特許番号
US07276528B2

反応ノート

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