Reserpine → 4-Bromo-2-chloro-1-phenoxybenzene

HRID 51575

반응식

HRID 51575 반응식
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[C:4]([Cl:9])[CH:3]=1.[C:10]1(B(O)O)[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.C(N(CC)CC)C.CO[C@@H]1[C@@H](C(OC)=O)[C@@H]2[C@@H](CN3[C@H](C2)C2NC4C=C(OC)C=CC=4C=2CC3)C[C@H]1OC(C1C=C(OC)C(OC)=C(OC)C=1)=O>ClCCl.CCCCCCC.C([O-])(=O)C.[Cu+2].C([O-])(=O)C.C(#N)C>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[C:4]([Cl:9])[CH:3]=1

참가 물질

9

반응물 4

HCID 5770ReserpineHCID 8471TriethylamineHCID 198594-Bromo-2-chlorophenolHCID 66827Phenylboronic Acid

생성물 1

HCID 227363094-Bromo-2-chloro-1-phenoxybenzene

시약·촉매·용매 4

HCID 8895Cupric acetate촉매HCID 6342Acetonitrile용매HCID 6344Dichloromethane용매HCID 8900Heptane용매

실험 절차

A mixture of 4-bromo-2-chlorophenol (2.07 g, 10 mmol), phenyl boronic acid (3.66 g, 30 mmol), copper(II) acetate (2.0 g, 1.1 mmol) and 4A powdered molecular sieves (20 g) in dichloromethane (100 mL) was treated with triethylamine (5.0 g, 50 mmol) then stirred at ambient temperature for 5 days. The mixture was diluted with heptane (100 mL), then filtered through a bed of celite. The filtrate was concentrated under reduced pressure to remove dichloromethane. The mixture was extracted with IN hydrochloric acid, 15 wt % aqueous sodium hydroxide, brine and then dried over magnesium sulfate. The mixture was filtered and the filtrate concentrated under reduced pressure to provide (1.27 g, 45%): 1H NMR (DMSO-d6, 400 MHz) δ 7.87(s, 1H), 7.55(d, 1H), 7.40(t, 2H), 7.17(t, 1H), 6.99(m, 3H); MS MH+283; RP-HPLC (Hypersil HS, 5 μm, 100 A 4.6×250 mm; 25%-100% acetonitrile—0.05 M ammonium acetate over 10 min, 1 m/min) tr 14.42min.

후처리

  1. filtrationfiltered through a bed of celite
  2. concentrationThe filtrate was concentrated under reduced pressure
  3. customto remove dichloromethane
  4. extractionThe mixture was extracted with IN hydrochloric acid, 15 wt % aqueous sodium hydroxide, brine
  5. dry with materialdried over magnesium sulfate
  6. filtrationThe mixture was filtered
  7. concentrationthe filtrate concentrated under reduced pressure
  8. customto provide (1.27 g, 45%)
  9. customtr 14.42min.

출처 및 근거

ORD 기록
ord-11c4d1aba29d43eb826cea2fa995c699
출처 데이터셋
uspto-grants-2004_03
특허 번호
US06713474B2

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