Sodium borohydride → 3-(4-Bromophenoxy)-6-methoxybenzo[b]thiophene 1,1-dioxide

HRID 632625Notes

Reaction equation

HRID 632625 reaction equation
Br[C:2]1[S:6](=[O:8])(=[O:7])[C:5]2[CH:9]=[C:10]([O:13][CH3:14])[CH:11]=[CH:12][C:4]=2[C:3]=1[O:15][C:16]1[CH:21]=[CH:20][C:19]([Br:22])=[CH:18][CH:17]=1.[BH4-].[Na+]>CO.CS(C)=O>[Br:22][C:19]1[CH:20]=[CH:21][C:16]([O:15][C:3]2[C:4]3[CH:12]=[CH:11][C:10]([O:13][CH3:14])=[CH:9][C:5]=3[S:6](=[O:8])(=[O:7])[CH:2]=2)=[CH:17][CH:18]=1

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 867306362-Bromo-3-(4-bromophenoxy)-6-methoxybenzo[b]thiophene 1,1-dioxide

Product 1

HCID 867306373-(4-Bromophenoxy)-6-methoxybenzo[b]thiophene 1,1-dioxideYield 97%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 887MethanolSolvent

Procedure

To a solution of 2-bromo-3-(4-bromophenoxy)-6-methoxy-benzo[b]thiophene 1,1-dioxide (3.10 g, 6.95 mmol) in MeOH (10 mL) and DMSO (30 mL) was added NaBH4 (0.789 g, 20.85 mmol). The mixture was stirred at room temperature for 3 h after which time the reaction was quenched with water and diluted with DCM. The organic layer was collected (phase separator) and concentrated to provide 3-(4-bromophenoxy)-6-methoxybenzo[b]thiophene 1,1-dioxide (2.47 g, 6.73 mmol 97% yield) as an off white solid which was used without further purification. 1H NMR (400 MHz, CDCl3) δ ppm=3.85 (s, 3 H), 5.38 (s, 1 H), 7.02-7.08 (m, 3 H), 7.22 (d, J=2.53 Hz, 1 H), 7.47-7.60 (m, 3 H).

Workup

  1. customwas quenched with water
  2. additiondiluted with DCM
  3. customThe organic layer was collected (phase separator)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-7e0411be5d6c469581b6952ad14e46a0
Source dataset
uspto-grants-2016_04
Patent number
US09321746B2

Reaction notes

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