Sodium Carbonate → HCID 4130341, compound

HRID 1272206Notes

Reaction equation

HRID 1272206 reaction equation
Br[C:2]1[CH:6]=[CH:5][S:4][CH:3]=1.[CH3:7][O:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1B(O)O.C(=O)([O-])[O-].[Na+].[Na+]>O1CCOCC1.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[S:4]1[CH:5]=[CH:6][C:2]([C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=2[O:8][CH3:7])=[CH:3]1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 133833-BromothiopheneHCID 27339582-Methoxyphenylboronic acid

Product 1

HCID 4130341HCID 4130341, compound

Reagents, catalysts & solvents 2

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 312751,4-DioxaneSolvent

Procedure

A solution of 3-bromothiophene (978 mg, 6 mmol) in 50 ml of dioxane is degassed with argon. Tetrakis-(triphenylphosphine)-palladium(0) (700 mg, 0.6 mmol) is added and the mixture is stirred for 5 minutes. 2-Methoxybenzene boronic acid (1.824 g, 12 mmol) and 12 ml of aqueous 2 N sodium carbonate are successively added and the resulting mixture is stirred for 16 hours at 85° C. The mixture is allowed to cool to room temperature then is extracted with dichloromethane (2×50 ml). The organic extracts are washed with water (2×30 ml) then dried over sodium sulfate, filtrated and evaporated. The residue is purified via flash column on silica (eluent: hexane/ethyl acetate 99:1 gradient to give 2-(thien-3-yl)anisole.

Workup

  1. stirringthe resulting mixture is stirred for 16 hours at 85° C
  2. extractionthen is extracted with dichloromethane (2×50 ml)
  3. washThe organic extracts are washed with water (2×30 ml)
  4. dry with materialthen dried over sodium sulfate
  5. filtrationfiltrated
  6. customevaporated
  7. customThe residue is purified via flash column on silica (eluent

Sources & evidence

ORD record
ord-e491886a07174e9ea756954f83ca1bc9
Source dataset
uspto-grants-2007_04
Patent number
US07208505B2

Reaction notes

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