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

HRID 606790Notes

Reaction equation

HRID 606790 reaction equation
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

Participants

6

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178419050HCID 178419050, compoundCatalystHCID 8471TriethylamineSolvent

Conditions

Temperature
90 °C

Procedure

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%).

Workup

  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

Sources & evidence

ORD record
ord-bf50737988824fb38228afe636909a32
Source dataset
uspto-grants-2011_03
Patent number
US07915424B2

Reaction notes

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