HCID 11265458, compound → HCID 11436844, compound

HRID 413015Notes

Reaction equation

HRID 413015 reaction equation
[CH3:1]C(C)([O-])C.[K+].[Br:7][C:8]1[C:9]([O:18][CH3:19])=[C:10]([C:13]([S:16][CH3:17])=[CH:14][CH:15]=1)[CH:11]=O>[Br-].C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C1COCC1>[Br:7][C:8]1[CH:15]=[CH:14][C:13]([S:16][CH3:17])=[C:10]([CH:11]=[CH2:1])[C:9]=1[O:18][CH3:19]

Participants

5

Reactant 2

HCID 11265458HCID 11265458, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 11436844HCID 11436844, compound

Reagents, catalysts & solvents 2

HCID 74505Methyltriphenyliphosphonium bromideCatalystHCID 8028TetrahydrofuranSolvent2×

Procedure

At 0° C., potassium tert-butoxide (6.2 g, 55.4 mmol) was added to a solution of methyltriphenylphosphoniumbromide (19.7 g, 55.4 mmol) in THF (180 ml). At from −10 to −5° C., 3-bromo-2-methoxy-6-methylsulfanylbenzaldehyde (12 g, 46 mmol) dissolved in THF (180 ml) was then added, and the mixture was stirred overnight at RT for 7 h. The mixture was filtered, and the solution was admixed with H2O (200 ml) and MTBE (200 ml) and then extracted with MTBE (200 ml). The combined organic phases were dried over MgSO4 and concentrated. Chromatography (cyclohexane→cyclohexane/EtOAc 9:1) gave 1-bromo-2-methoxy-4-methylsulfanyl-3-vinylbenzene.

Workup

  1. additionwas then added
  2. filtrationThe mixture was filtered
  3. extractionextracted with MTBE (200 ml)
  4. dry with materialThe combined organic phases were dried over MgSO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-81860cb109704a1dbe60468dcc2ceaf1
Source dataset
uspto-grants-2003_05
Patent number
US06566307B1

Reaction notes

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