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

HRID 270161

反応式

HRID 270161 の反応式
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

参加物

8

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 80271Tri-o-tolylphosphine触媒3 回HCID 167845palladium(II) acetate触媒3 回HCID 8471Triethylamine溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-8bcff28ad0e14b338a260eb9926ea3ba
出典データセット
uspto-grants-2008_11
特許番号
US07449495B2

関連ノート

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