4,4,5,5-Tetramethyl[1,3,2]dioxaborolane → 2-(2-(Butyloxy)-5-(methyloxy)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

HRID 2101748노트

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HRID 2101748 반응식
Br[C:2]1[CH:7]=[C:6]([O:8][CH3:9])[CH:5]=[CH:4][C:3]=1[O:10][CH2:11][CH2:12][CH2:13][CH3:14].O(C1C=CC=CC=1P(C1C=CC=CC=1)C1C=CC=CC=1)C1C=CC=CC=1P(C1C=CC=CC=1)C1C=CC=CC=1.[CH3:54][C:55]1([CH3:62])[C:59]([CH3:61])([CH3:60])[O:58][BH:57][O:56]1>O1CCOCC1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH2:11]([O:10][C:3]1[CH:4]=[CH:5][C:6]([O:8][CH3:9])=[CH:7][C:2]=1[B:57]1[O:58][C:59]([CH3:61])([CH3:60])[C:55]([CH3:62])([CH3:54])[O:56]1)[CH2:12][CH2:13][CH3:14]

참가 물질

6

반응물 3

HCID 27347684,4,5,5-Tetramethyl[1,3,2]dioxaborolaneHCID 4285986Bis[2-(diphenylphosphino)phenyl] etherHCID 578018162-Bromo-1-butoxy-4-methoxybenzene

생성물 1

HCID 576724442-(2-(Butyloxy)-5-(methyloxy)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane수율 41%

시약·촉매·용매 2

HCID 167845palladium(II) acetate촉매HCID 312751,4-Dioxane용매

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온도
95 °C

실험 절차

A mixture of 2-bromo-1-butoxy-4-methoxybenzene (1.2 g, 4.7 mmol), TEA (2.6 mL, 19 mmol), (oxydi-2,1-phenylene)bis(diphenylphosphine) (0.51 g, 0.95 mmol) (Aldrich, CAS# 166330-10-5), palladium(II) acetate (0.11 g, 0.47 mmol), and 4,4,5,5-tetramethyl-1,3,2-dioxaborolane (2.1 mL, 14 mmol) (Aldrich, CAS# 25015-63-8) in 1,4-dioxane (5.0 mL) was stirred overnight at 95° C. The mixture was cooled to room temperature, quenched with saturated aqueous ammonium chloride, and extracted with ether. The combined organic layers were dried over MgSO4 and concentrated. The crude product was purified by silica gel flash chromatography (0-10% EtOAc/hexane) to afford compound C.3 (0.60 g, 41% yield) as a colorless oil. 1H NMR (400 MHz, CDCl3) δ 7.16 (d, J=3.1 Hz, 1H), 6.91 (dd, J=3.1, 9.0 Hz, 1H), 6.79 (d, J=9.0 Hz, 1H), 3.91 (t, J=6.3 Hz, 2H), 3.78 (s, 3H), 1.75 (m, 2H), 1.54 (m, 2H), 1.34 (s, 12H), 0.96 (t, J=7.4, 3H).

후처리

  1. temperatureThe mixture was cooled to room temperature
  2. customquenched with saturated aqueous ammonium chloride
  3. extractionextracted with ether
  4. dry with materialThe combined organic layers were dried over MgSO4
  5. concentrationconcentrated
  6. customThe crude product was purified by silica gel flash chromatography (0-10% EtOAc/hexane)
  7. customto afford compound C.3 (0.60 g, 41% yield) as a colorless oil

출처 및 근거

ORD 기록
ord-e64b106892d4477aba7d7786c397c676
출처 데이터셋
uspto-grants-2009_08
특허 번호
US07572934B2

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