Hydrochloric Acid → Methyl (E)-3-(4'-hydroxy-[1,1'-biphenyl]-4-yl)acrylate

HRID 270161

반응식

HRID 270161 반응식
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([OH:14])=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.[C:15]([O:19][CH3:20])(=[O:18])[CH:16]=[CH2:17].Cl.C(OCC)(=O)C>C(N(CC)CC)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C>[OH:14][C:11]1[CH:12]=[CH:13][C:8]([C:5]2[CH:6]=[CH:7][C:2](/[CH:17]=[CH:16]/[C:15]([O:19][CH3:20])=[O:18])=[CH:3][CH:4]=2)=[CH:9][CH:10]=1

참가 물질

8

반응물 4

HCID 313Hydrochloric AcidHCID 7294Methyl AcrylateHCID 8857Ethyl AcetateHCID 950934-Bromo-4'-hydroxybiphenyl

생성물 1

HCID 9943013Methyl (E)-3-(4'-hydroxy-[1,1'-biphenyl]-4-yl)acrylate수율 83.3%

시약·촉매·용매 3

HCID 80271Tri-o-tolylphosphine촉매3회HCID 167845palladium(II) acetate촉매3회HCID 8471Triethylamine용매

실험 절차

A mixture of 2 g (8.03 mmol) of 4-(4-bromophenyl)phenol, 1.1 g (12.8 mmol) of methyl acrylate, 18 mg (0.08 mmol) of Palladium acetate, and 94 mg (0.31 mmol) of tri-(o-tolyl)phosphine in 3.7 ml of triethylamine was refluxed for 6 hours. A further 6 mg of Palladium acetate and 30 mg of tri-(o-tolyl)phosphine were added and heated for an hour, then a further 30 mg of Palladium acetate and 94 mg di tri-(o-toluyl)phosphine were added and heated for 3.5 hours. Then the reaction was acidified with 6M HCl, ethyl acetate was added, and stirred for a time to dissolve the precipitate, the phases were separated, the organic phase dried over Na2SO4 and the solvent evaporated. The crude product (934 mg) was purified by taking up in hexane/ethyl ether and filtered off to give 1.7 g of the title product.

후처리

  1. temperaturewas refluxed for 6 hours
  2. temperatureheated for an hour
  3. temperatureheated for 3.5 hours
  4. additionwas added
  5. dissolutionto dissolve the precipitate
  6. customthe phases were separated
  7. dry with materialthe organic phase dried over Na2SO4
  8. customthe solvent evaporated
  9. customThe crude product (934 mg) was purified
  10. filtrationfiltered off

출처 및 근거

ORD 기록
ord-8bcff28ad0e14b338a260eb9926ea3ba
출처 데이터셋
uspto-grants-2008_11
특허 번호
US07449495B2

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