Water → HCID 66857173, compound

HRID 252253Notes

Reaction equation

HRID 252253 reaction equation
Br[C:2]1[S:3][CH:4]=[CH:5][C:6]=1[CH3:7].[CH3:8][O:9][C:10]1[CH:15]=[CH:14][C:13](B(O)O)=[CH:12][CH:11]=1.C([O-])([O-])=O.[Na+].[Na+].O>O1CCOCC1.COC(C)(C)C.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:8][O:9][C:10]1[CH:15]=[CH:14][C:13]([C:2]2[S:3][CH:4]=[CH:5][C:6]=2[CH3:7])=[CH:12][CH:11]=1

Participants

8

Reactant 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 843142-Bromo-3-methylthiopheneHCID 201262(4-Methoxyphenyl)boronic acid

Product 1

HCID 66857173HCID 66857173, compound

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 15413tert-Butyl methyl etherSolventHCID 312751,4-DioxaneSolvent

Procedure

2-Bromo-3-methyl-thiophene (0.53 g, 3.00 mmol) was dissolved in 1,4-dioxane (35 ml) under an argon atmosphere. To this solution were added Pd(PPh3)4 (0.33 g, 0.28 mmol), 4-methoxyphenyl boronic acid (0.50 g, 3.30 mmol) and 2 M Na2CO3 (6 ml). The resultant mixture was stirred at 100° C. for 2 hours. The reaction was cooled to rt diluted with tert.butyl methyl ether and poured into water and extracted with tert.butyl methyl ether (2×). The combined organic extracts were washed with water, brine, dried (MgSO4.2H2O), filtered and concentrated under reduced pressure to yield a yellow oil that was purified over silica gel (n-heptane) to yield an oil: 0.32 g (48%), GC-MS: M=204.

Workup

  1. extractionextracted with tert.butyl methyl ether (2×)
  2. washThe combined organic extracts were washed with water, brine
  3. dry with materialdried (MgSO4.2H2O)
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customto yield a yellow oil that
  7. customwas purified over silica gel (n-heptane)
  8. customto yield an oil

Sources & evidence

ORD record
ord-c481b284a23344389a55d2b966b7a69d
Source dataset
uspto-grants-2011_01
Patent number
US07868030B2

Reaction notes

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