1-Bromo-3-chlorobenzene → 4-(3-Chlorophenyl)-2-methyl-3-butyn-2-ol

HRID 606790노트

반응식

HRID 606790 반응식
Br[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[CH:3]=1.[CH3:9][C:10]([OH:14])([C:12]#[CH:13])[CH3:11]>C1(C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)[Pd][P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[Cu]I.C(N(CC)CC)C>[Cl:8][C:4]1[CH:3]=[C:2]([C:13]#[C:12][C:10]([CH3:11])([OH:14])[CH3:9])[CH:7]=[CH:6][CH:5]=1

참가 물질

6

반응물 2

HCID 79281-Bromo-3-chlorobenzeneHCID 82582-Methyl-3-butyn-2-ol

생성물 1

HCID 230063744-(3-Chlorophenyl)-2-methyl-3-butyn-2-ol수율 94%

시약·촉매·용매 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 178419050HCID 178419050, 화합물촉매HCID 8471Triethylamine용매

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온도
90 °C

실험 절차

Add triethylamine (75 mL), 1-bromo-3-chlorobenzene (24.1 g, 0.126 mol), and 2-methylbut-3-yn-2-ol (15 mL, 0.152 mol) to a degassed mixture of bis(triphenylphosphine)palladium (II) dichloride (49 mg, 7.1 10−5 mol) and copper (I) iodide (2.4 mg, 1.26 10−5 mol). Stir at 90° C. for 72 h. Cool the reaction mixture to room temperature. Filter, concentrate and dissolve in ethyl acetate. Wash with water and dry the organic phase over sodium sulfate. Filter, concentrate and purify the residue by silica gel chromatography, eluting with hexane:ethyl acetate 6:1, to give the title compound (23 g, 94%).

후처리

  1. temperatureCool the reaction mixture to room temperature
  2. filtrationFilter
  3. concentrationconcentrate
  4. dissolutiondissolve in ethyl acetate
  5. washWash with water
  6. dry with materialdry the organic phase over sodium sulfate
  7. filtrationFilter
  8. concentrationconcentrate
  9. custompurify the residue by silica gel chromatography
  10. washeluting with hexane:ethyl acetate 6:1

출처 및 근거

ORD 기록
ord-bf50737988824fb38228afe636909a32
출처 데이터셋
uspto-grants-2011_03
특허 번호
US07915424B2

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