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

HRID 1391735노트

반응식

HRID 1391735 반응식
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]

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 178418397HCID 178418397, 화합물촉매HCID 80711,2-Dimethoxyethane용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-ea2239c295554a4487bd1267e24c1002
출처 데이터셋
uspto-grants-2008_03
특허 번호
US07338960B2

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