Potassium Carbonate → Ethyl 5-chloro-2''-[(phenylmethyl)oxy]-1,1':2',1''-terphenyl-2-carboxylate

HRID 269565

반응식

HRID 269565 반응식
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[C:15]1[C:16](B(O)O)=[CH:17][CH:18]=[CH:19][CH:20]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Br[C:25]1[CH:35]=[C:34]([Cl:36])[CH:33]=[CH:32][C:26]=1[C:27]([O:29][CH2:30][CH3:31])=[O:28].C(=O)([O-])[O-].[K+].[K+].C1(C)C=CC=CC=1.C(O)C>C(OCC)C.O.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>[Cl:36][C:34]1[CH:33]=[C:32]([C:16]2[C:15]([C:10]3[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=3[O:8][CH2:1][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:26]([C:27]([O:29][CH2:30][CH3:31])=[O:28])=[CH:25][CH:35]=1

참가 물질

8

반응물 4

HCID 11430Potassium CarbonateHCID 21863594Toluene ethanolHCID 53216606Ethyl 2-bromo-4-chlorobenzoateHCID 587309902'-Benzyloxy-biphenyl-2-boronic acid

생성물 1

HCID 58731013Ethyl 5-chloro-2''-[(phenylmethyl)oxy]-1,1':2',1''-terphenyl-2-carboxylate

시약·촉매·용매 3

HCID 178418397HCID 178418397, 화합물촉매HCID 962Water용매HCID 3283Diethyl Ether용매

반응 조건

온도
90 °C

실험 절차

A mixture of 2′-benzyloxybiphenyl boronic acid (50 mg, 0.16 mmol), ethyl 2-bromo-4-chlorobenzoate (66 mg, 0.25 mmol), potassium carbonate (88 mg, 0.64 mmol) and tetrakis(triphenylphosphine)palladium(0) (10 mg, 5 mol %) in 1:1 toluene/ethanol (2 ml) was stirred and heated at 90° C. under nitrogen for 12 hours. After cooling the mixture was diluted with diethyl ether and water and the organic phase dried (MgSO4) and evaporated to dryness. The residue was chromatographed with ethyl acetate/iso-hexane (1:9) to yield the title compound as a pale yellow gum. (46 mg, 66%).

후처리

  1. temperatureAfter cooling the mixture
  2. dry with materialthe organic phase dried (MgSO4)
  3. customevaporated to dryness
  4. customThe residue was chromatographed with ethyl acetate/iso-hexane (1:9)

출처 및 근거

ORD 기록
ord-a36b5c992b014a60a613a74fb93c144b
출처 데이터셋
uspto-grants-2008_11
특허 번호
US07446222B2

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