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

HRID 606790ノート

反応式

HRID 606790 の反応式
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

参加物

6

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 178419050HCID 178419050、化合物触媒HCID 8471Triethylamine溶媒

反応条件

温度
90 °C

実験手順

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%).

後処理

  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

出典と根拠

ORDレコード
ord-bf50737988824fb38228afe636909a32
出典データセット
uspto-grants-2011_03
特許番号
US07915424B2

反応ノート

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