Methanol → HCID 53739261, 화합물

HRID 226054노트

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HRID 226054 반응식
Br[C:2]1[C:7]2[S:8][C:9]([CH3:11])=[CH:10][C:6]=2[CH:5]=[CH:4][CH:3]=1.CCN(CC)CC.CO.C[CH2:22][O:23][C:24](C)=[O:25]>CS(C)=O.CC([O-])=O.CC([O-])=O.[Pd+2].C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.[Fe+2]>[CH3:22][O:23][C:24]([C:2]1[C:7]2[S:8][C:9]([CH3:11])=[CH:10][C:6]=2[CH:5]=[CH:4][CH:3]=1)=[O:25]

참가 물질

8

반응물 4

HCID 887MethanolHCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 126238737-Bromo-2-methyl-1-benzothiophene

생성물 1

HCID 53739261HCID 53739261, 화합물수율 82%

시약·촉매·용매 3

HCID 167845palladium(II) acetate촉매HCID 635956Ferrocene-1,1'-bis-(diphenylphosphine)촉매HCID 679Dimethyl Sulfoxide용매

실험 절차

A mixture of 7-bromo-2-methyl-benzo[b]thiophene (Acheson, R. M.; Cooper, M. W. J. Chem. Soc., Perkin Trans 11980, 1185), (0.88 g, 3.89 mmol), with Pd(OAc)2 (176.4 mg), dppf (637.2 mg), Et3N (3.0 mL) and CH3OH (17 mL) in DMSO (26 mL) is reacted at 80° C./1100 psi of CO for 24 h. The crude reaction mixture is diluted with EtOAc (100 mL), washed with 0.1 M HCl (3×30 mL); dried with Na2SO4; filtered and concentrated. Purification of the crude material by silica gel chromatography to give the title compound (0.66 g, 3.19 mmol, 82%). 1H NMR (CDCl3): δ 2.63 (s, 3H), 4.02 (s, 3H), 7.04 (q, J=0.9 Hz, 1H), 7.38 (t, J=7.9 Hz, 1H), 7.84 (d, J=8.0 Hz, 1H), 8.01 (dd, J=8.0, 1.3 Hz, 1H) ppm. ES-MS (m/z): calcd for C11H10O2S (M+NH4)+: 224.3. found: 224.1.

후처리

  1. customThe crude reaction mixture
  2. washwashed with 0.1 M HCl (3×30 mL)
  3. dry with materialdried with Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customPurification of the crude material by silica gel chromatography

출처 및 근거

ORD 기록
ord-15c9ee534e3c41aba5e25f1d3aa3f8c5
출처 데이터셋
uspto-grants-2009_07
특허 번호
US07557103B2

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