Bromobenzene → 2-Phenylthiopyrrole

HRID 1936557Notes

Reaction equation

HRID 1936557 reaction equation
[C:1]1([Mg]Br)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.BrC1C=CC=CC=1.[Mg].[S:17]([C:20]1[NH:21][CH:22]=[CH:23][CH:24]=1)C#N>C1COCC1>[C:1]1([S:17][C:20]2[NH:21][CH:22]=[CH:23][CH:24]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 4

HCID 7961BromobenzeneHCID 5462224MagnesiumHCID 126747602-Thiocyanato-1H-pyrroleHCID 178418255HCID 178418255, compound

Product 1

HCID 127893912-PhenylthiopyrroleYield 93%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

To a solution of phenyl magnesium bromide (prepared from bromobenzene (0.75 ml) and magnesium chips (0.19 g, 7.8 mmol) in anhydrous THF (20 ml), cooled to 0° C., was slowly added a solution of 2-thiocyanopyrrole 11 (0.5 g, 4.0 mmol) in anhydrous THF (20 ml). After stirring at 0° C. for 30 min, the mixture was poured into crushed ice and extracted with ethyl acetate. The organic phase was washed with 20% NH4Cl, anhydrified and evaporated. The residue was purified by chromatography (35% hexane in chloroform) to give 0.6 g (93% yield) of 12 as colourless prisms: melting point 86-87° C. (hexane); IR (CHCl3) 3420 cm−1; 1H NMR (CDCl3) δ8.20 (br s, 1H), 7.25-6.85 (m, 5H), 6.92 (m, 1H), 6.55 (m, 1H), 6.31 (m, 1H). Anal. (C9H9NS): C, H, N.

Workup

  1. additionthe mixture was poured
  2. custominto crushed ice
  3. extractionextracted with ethyl acetate
  4. washThe organic phase was washed with 20% NH4Cl
  5. customevaporated
  6. customThe residue was purified by chromatography (35% hexane in chloroform)

Sources & evidence

ORD record
ord-dd748329fa884101b198ed4b62bc7753
Source dataset
uspto-grants-2002_05
Patent number
US06391870B2

Reaction notes

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