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

HRID 51575

反応式

HRID 51575 の反応式
[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

参加物

9

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 4

HCID 8895Cupric acetate触媒HCID 6342Acetonitrile溶媒HCID 6344Dichloromethane溶媒HCID 8900Heptane溶媒

実験手順

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.

後処理

  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.

出典と根拠

ORDレコード
ord-11c4d1aba29d43eb826cea2fa995c699
出典データセット
uspto-grants-2004_03
特許番号
US06713474B2

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