Water → [(2-Methyl-4-{2-[4'-(trifluoromethyl)-3-biphenylyl]ethenyl}phenyl)oxy]acetic acid

HRID 1391735ノート

反応式

HRID 1391735 の反応式
Br[C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]2[CH:15]=[CH:14][C:13]([O:16][CH2:17][C:18]([O:20]CC)=[O:19])=[C:12]([CH3:23])[CH:11]=2)[CH:5]=[CH:6][CH:7]=1.C([O-])([O-])=O.[Na+].[Na+].[F:30][C:31]([F:42])([F:41])[C:32]1[CH:37]=[CH:36][C:35](B(O)O)=[CH:34][CH:33]=1.O>COCCOC.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>[CH3:23][C:12]1[CH:11]=[C:10]([CH:9]=[CH:8][C:4]2[CH:3]=[C:2]([C:35]3[CH:36]=[CH:37][C:32]([C:31]([F:42])([F:41])[F:30])=[CH:33][CH:34]=3)[CH:7]=[CH:6][CH:5]=2)[CH:15]=[CH:14][C:13]=1[O:16][CH2:17][C:18]([OH:20])=[O:19]

参加物

7

反応物 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 27343894-(Trifluoromethyl)phenylboronic acidHCID 76843166Ethyl ({4-[2-(3-bromophenyl)ethenyl]-2-methylphenyl}oxy)acetate

生成物 1

HCID 69210988[(2-Methyl-4-{2-[4'-(trifluoromethyl)-3-biphenylyl]ethenyl}phenyl)oxy]acetic acid収率 57%

試薬・触媒・溶媒 2

HCID 178418397HCID 178418397、化合物触媒HCID 80711,2-Dimethoxyethane溶媒

実験手順

Ethyl ({4-[2-(3-bromophenyl)ethenyl]-2-methylphenyl}oxy)acetate (150 mg, 0.40 mmol), Na2CO3 (106 mg, 1.00 mmol), 4-(triflouromethyl)benzeneboronic acid (83.5 mg, 0.44 mmol) and Pd(PPh3)4 (23 mg, 0.02 mmol) was dissolved in DME and water (2:1, 6 mL) and the mixture heated at reflux for 4 hours. The mixture was allowed to cool to rt, was concentrated under reduced pressure and the residue partitioned between EtOAc (15 mL) and water (15 mL). The aqueous layer was then acidified with aqueous HCl (1N) and extracted with EtOAc and the combined organic layers dried (MgSO4), filtered and reduced to give the title compound (94 mg).

後処理

  1. temperatureat reflux for 4 hours
  2. concentrationwas concentrated under reduced pressure
  3. customthe residue partitioned between EtOAc (15 mL) and water (15 mL)
  4. extractionextracted with EtOAc
  5. dry with materialthe combined organic layers dried (MgSO4)
  6. filtrationfiltered

出典と根拠

ORDレコード
ord-ea2239c295554a4487bd1267e24c1002
出典データセット
uspto-grants-2008_03
特許番号
US07338960B2

反応ノート

読み込み中…