2-Bromophenol → 1-Bromo-2-(2-ethylphenoxy)benzene

HRID 253554

반응식

HRID 253554 반응식
[CH2:1]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1B(O)O)[CH3:2].[Br:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[OH:19].CCN(CC)CC>C(Cl)Cl.CC([O-])=O.CC([O-])=O.[Cu+2]>[Br:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[O:19][C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=1[CH2:1][CH3:2]

참가 물질

6

반응물 3

HCID 72442-BromophenolHCID 8471TriethylamineHCID 41008622-Ethylphenylboronic Acid (contains varying amounts of Anhydride)

생성물 1

HCID 574196131-Bromo-2-(2-ethylphenoxy)benzene수율 31%

시약·촉매·용매 2

HCID 8895Cupric acetate촉매HCID 6344Dichloromethane용매

실험 절차

To a solution of 2-ethylphenylboronic acid (4.50 g, 30 mmol), 2-bromophenol (3.54 g, 20 mmol), and Cu(OAc)2 (1.86 g, 10 mmol) in anhydrous CH2Cl2 (50 mL) were added activated 4 Å molecular sieves (˜0.5 g), followed by anhydrous Et3N (7.0 mL, 50 mmol). The resulting dark green solution was stirred at rt for 48 h. The solvent was removed under vacuum and the residue was triturated several times with ether (˜200 mL). The combined organic solutions were washed with satd aq NH4Cl, and 1 N aq HCl aqueous solution, and solvent was removed under vacuum to give a crude product. Flash column chromatography gave 1-bromo-2-(2-ethylphenoxy)benzene (1.72 g, 31%) as a clear oil; 1H NMR (CDCl3, 400 MHz) δ: 7.62 (dd, 1H), 7.28 (m, 1H), 7.22-7.08 (m, 3H), 6.96 (m, 1H), 6.78 (m, 2H), 2.64 (q, 2H), 1.22 (t, 3H); MS no ionization was observed.

후처리

  1. customThe solvent was removed under vacuum
  2. customthe residue was triturated several times with ether (˜200 mL)
  3. washThe combined organic solutions were washed with satd aq NH4Cl, and 1 N aq HCl aqueous solution, and solvent
  4. customwas removed under vacuum
  5. customto give a crude product

출처 및 근거

ORD 기록
ord-43699f6428104e0ebb0068ca970a8f32
출처 데이터셋
uspto-grants-2011_01
특허 번호
US07872028B2

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