Cyclohexanethiol → HCID 70873927, compound

HRID 2208952Notes

Reaction equation

HRID 2208952 reaction equation
Br[C:2]1[C:3]([CH3:13])=[C:4]([CH:9]=[C:10]([Cl:12])[CH:11]=1)[C:5]([O:7][CH3:8])=[O:6].C(N(CC)C(C)C)(C)C.CC1(C)C2C(=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=CC=2)OC2C(P(C3C=CC=CC=3)C3C=CC=CC=3)=CC=CC1=2.[CH2:65]1[CH2:70][CH2:69][CH:68]([SH:71])[CH2:67][CH2:66]1>O1CCOCC1.CC([O-])=O.CC([O-])=O.[Pd+2]>[Cl:12][C:10]1[CH:11]=[C:2]([S:71][CH:68]2[CH2:69][CH2:70][CH2:65][CH2:66][CH2:67]2)[C:3]([CH3:13])=[C:4]([CH:9]=1)[C:5]([O:7][CH3:8])=[O:6]

Participants

7

Reactant 4

HCID 15290CyclohexanethiolHCID 81531DiisopropylethylamineHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 70874048methyl 3-bromo-5-chloro-2-methylbenzoate

Product 1

HCID 70873927HCID 70873927, compoundYield 88.3%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 312751,4-DioxaneSolvent

Procedure

To a stirred solution of methyl 3-bromo-5-chloro-2-methylbenzoate (1.0 g, 3.79 mmol) in 1,4-dioxane was added N,N-diisopropyl ethylamine (0.98 g, 7.59 mmol). The reaction mixture was purged with argon for 20 min. then Pd(OAc)2 (0.042 g, 0.189 mmol), Xanthphos (0.22 g, 0.38 mmol) and cyclohexylthiol (0.44 g, 3.79 mmol) was added to it sequentially and again purged with argon for 10 min. The reaction mixture was then refluxed for 16 h. On completion, water was added, and the product extracted with ethyl acetate. The organic layer was dried over sodium sulphate and the product was purified by silica gel column to afford the title compound (1.0 g, 83%)

Workup

  1. customThe reaction mixture was purged with argon for 20 min.
  2. customagain purged with argon for 10 min
  3. temperatureThe reaction mixture was then refluxed for 16 h
  4. additionOn completion, water was added
  5. extractionthe product extracted with ethyl acetate
  6. dry with materialThe organic layer was dried over sodium sulphate
  7. customthe product was purified by silica gel column

Sources & evidence

ORD record
ord-d1b8019c6f4d4700975b70e9187eb820
Source dataset
uspto-grants-2016_06
Patent number
US09376422B2

Reaction notes

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