Bromine → 3-Bromo-6-fluoro-1-(phenylsulfonyl)-1H-indole

HRID 2274757Notes

Reaction equation

HRID 2274757 reaction equation
[F:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[CH:7][N:8]2[S:11]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)(=[O:13])=[O:12])=[CH:4][CH:3]=1.[Br:20]Br.[O-]S([O-])(=S)=O.[Na+].[Na+]>C(Cl)Cl>[Br:20][C:6]1[C:5]2[C:9](=[CH:10][C:2]([F:1])=[CH:3][CH:4]=2)[N:8]([S:11]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)(=[O:13])=[O:12])[CH:7]=1

Participants

5

Reactant 3

HCID 24408BromineHCID 24477Sodium ThiosulfateHCID 112543626-Fluoro-1-(phenylsulfonyl)-1h-indole2×

Product 1

HCID 863462493-Bromo-6-fluoro-1-(phenylsulfonyl)-1H-indoleYield 99%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

To a solution of 6-fluoro-1-(phenylsulfonyl)-1H-indole (Intermediate 1; 1.0 g; 3.6 mmol) in DCM (20 mL) at 0° C. was added a solution of bromine (0.64 g; 4.0 mmol) in DCM (20 mL) dropwise. The mixture was stirred at 0° C. for 0.5 h, then added saturated aqueous Na2S2O3 (10 mL), and stirred at r.t. for 10 minute. The organic layer was separated and the aqueous layer was extracted with DCM (10 mL×2). The combined organic layers were washed with saturated aqueous NaHCO3 (20 mL×2), water (20 mL×2), brine (20 mL), dried over anhydrous Na2SO4, filtered, and concentrated to afford 1.26 g (99%) of the title compound as a pink solid.

Workup

  1. customThe organic layer was separated
  2. extractionthe aqueous layer was extracted with DCM (10 mL×2)
  3. washThe combined organic layers were washed with saturated aqueous NaHCO3 (20 mL×2), water (20 mL×2), brine (20 mL)
  4. dry with materialdried over anhydrous Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-99f37149c2184dd49ad55bacf6545dda
Source dataset
uspto-grants-2015_09
Patent number
US09126984B2

Reaction notes

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