Trimethyl orthoformate → 6-Bromo-5-chlorobenzoxazole

HRID 874604노트

반응식

HRID 874604 반응식
[NH2:1][C:2]1[CH:7]=[C:6]([Cl:8])[C:5]([Br:9])=[CH:4][C:3]=1[OH:10].[Yb+3].F[C:13](F)(F)S([O-])(=O)=O.FC(F)(F)S([O-])(=O)=O.FC(F)(F)S([O-])(=O)=O.C(OC)(OC)OC>CCO.CC(=O)OCC.CCCCCC>[Br:9][C:5]1[C:6]([Cl:8])=[CH:7][C:2]2[N:1]=[CH:13][O:10][C:3]=2[CH:4]=1

참가 물질

7

반응물 3

HCID 9005Trimethyl orthoformateHCID 2733225Ytterbium triflateHCID 584871002-Amino-5-bromo-4-chlorophenol

생성물 1

HCID 584872776-Bromo-5-chlorobenzoxazole수율 6,559.2%

시약·촉매·용매 3

HCID 702Ethanol용매HCID 8058Hexane용매HCID 8857Ethyl Acetate용매2회

반응 조건

온도
90 °C

실험 절차

A mixture of 2-amino-5-bromo-4-chlorophenol (29) (865 mg, 3.89 mmol), trifluoromethanesulfonic acid Ytterbium (III) salt (24 mg, 1% mol) and trimethyl orthoformate (511 μl, 1.2 eq.) in 2 ml EtOH was heated at 90° C. for 2 h. After cooling down to r.t., the reaction mixture was taken up in EA, washed with aq. NaHCO3 and brine, dried over Na2SO4, concentrated to dryness. The resulting brown solid was dissolved in DCM and subjected to silica gel column purification using 0-100% B (A: hexane; B: 50% EA in hexane) to furnish 590 mg 30 as yellow solid (yield: 65.2%).

후처리

  1. temperatureAfter cooling down to r.t.
  2. washwashed with aq. NaHCO3 and brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated to dryness
  5. dissolutionThe resulting brown solid was dissolved in DCM
  6. customsubjected to silica gel column purification

출처 및 근거

ORD 기록
ord-2c55f35bb8d9410eabf22e12ba737ad9
출처 데이터셋
uspto-grants-2015_03
특허 번호
US08980629B2

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