Triphenylphosphine → HCID 69586682, compound

HRID 723078Notes

Reaction equation

HRID 723078 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH3:20][O:21][C:22]([C:24]1[S:25][C:26]([N+:30]([O-:32])=[O:31])=[C:27](Br)[CH:28]=1)=[O:23].[CH3:33][C:34]1[C:39]([C:40]2[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=2)=[CH:38][C:37]([SH:46])=[CH:36][CH:35]=1>CN(C)C1C=CN=CC=1.C1COCC1>[CH3:20][O:21][C:22]([C:24]1[S:25][C:26]([N+:30]([O-:32])=[O:31])=[C:27]([S:46][C:37]2[CH:38]=[C:39]([C:40]3[CH:41]=[CH:42][CH:43]=[CH:44][CH:45]=3)[C:34]([CH3:33])=[CH:35][CH:36]=2)[CH:28]=1)=[O:23]

Participants

6

Reactant 3

HCID 11776TriphenylphosphineHCID 13291027Methyl 4-bromo-5-nitrothiophene-2-carboxylateHCID 21886332HCID 21886332, compound

Product 1

HCID 69586682HCID 69586682, compoundYield 61%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of triphenylphosphine (0.67 g, 2.55 mmol), 4-bromo-5-nitro-thiophene-2-carboxylic acid methyl ester ((Example 114, step c) 1 g, 3.76 mmol) and 4-(dimethyl)aminopyridine resin (1 eq) in THF was added 6-methyl-biphenyl-3-thiol from above step b. This mixture was stirred for 3 hrs. The reaction mixture was filtered and the solvents were removed in vacuo. The residue was purified via column chromatography (SiO2, 15% ethyl acetate/hexane) to afford a yellow glass (600 mg, 61%), which was used in the following step.

Workup

  1. filtrationThe reaction mixture was filtered
  2. customthe solvents were removed in vacuo
  3. customThe residue was purified via column chromatography (SiO2, 15% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-0dcd9d77d19d4ba4a35323356c08a79b
Source dataset
uspto-grants-2006_11
Patent number
US07138530B2

Reaction notes

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