Bromine → HCID 12088667, compound

HRID 650548Notes

Reaction equation

HRID 650548 reaction equation
[CH3:1][S:2]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[C:15]([C:16]3[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][CH:17]=3)=[CH:14][S:13][CH:12]=2)=[CH:7][CH:6]=1)(=[O:4])=[O:3].[Br:24]Br>C(O)(=O)C>[CH3:1][S:2]([C:5]1[CH:6]=[CH:7][C:8]([C:11]2[C:15]([C:16]3[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][CH:17]=3)=[C:14]([Br:24])[S:13][CH:12]=2)=[CH:9][CH:10]=1)(=[O:4])=[O:3]

Participants

4

Reactant 2

HCID 24408BromineHCID 15551254HCID 15551254, compound

Product 1

HCID 12088667HCID 12088667, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

3-(4-methylsulphonylphenyl)-4-(4-methoxyphenyl)thiophene from Example 6 (9.3 mg) was dissolved in acetic acid (10 ml) and heated to 90° C. at which time Br2 in acetic acid (1.0M, 27 μl) was added in one portion. The reaction was stirred for 15 minutes at which time the solvent was removed at reduced pressure. The residue was dissolved in a minimum of ethyl acetate and chromatographed on silica, eluting with 2.5% isopropanol in hexane, yielding 3-(4-methylsulfonylphenyl)-4-(4-methoxyphenyl)-5-bromothiophene. CI MS (M+H): 423/425.

Workup

  1. additionwas added in one portion
  2. customwas removed at reduced pressure
  3. dissolutionThe residue was dissolved in a minimum of ethyl acetate
  4. customchromatographed on silica
  5. washeluting with 2.5% isopropanol in hexane

Sources & evidence

ORD record
ord-4f123543743149c2a966431b8322e7a8
Source dataset
uspto-grants-2001_08
Patent number
US06274590B1

Reaction notes

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