4-Bromophenol → 2-Bromo-3-(4-bromophenoxy)-6-methoxybenzo[b]thiophene 1,1-dioxide

HRID 632708Notes

Reaction equation

HRID 632708 reaction equation
[Br:1][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]=1Br.[Br:16][C:17]1[CH:22]=[CH:21][C:20]([OH:23])=[CH:19][CH:18]=1.C([O-])([O-])=O.[Cs+].[Cs+]>C1COCC1>[Br:1][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:23][C:20]1[CH:21]=[CH:22][C:17]([Br:16])=[CH:18][CH:19]=1

Participants

5

Reactant 3

HCID 78084-BromophenolHCID 10796Cesium carbonateHCID 161275842,3-Dibromo-6-methoxybenzo[b]thiophene 1,1-dioxide

Product 1

HCID 867306362-Bromo-3-(4-bromophenoxy)-6-methoxybenzo[b]thiophene 1,1-dioxideYield 98.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2,3-dibromo-6-methoxybenzo[b]thiophene 1,1-dioxide (2.50 g, 7.06 mmol) in THF (100 mL) at room temperature was added 4-bromophenol (1.344 g, 7.77 mmol) and Cs2CO3 (6.90 g, 21.19 mmol). The reaction mixture turned green after −1 min of stirring. The mixture was stirred at room temperature for 18 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 2-bromo-3-(4-bromophenoxy)-6-methoxybenzo[b]thiophene 1,1-dioxide (3.10 g, 6.95 mmol, 98% yield) as a white solid which was used without further purification. 1H NMR (400 MHz, CDCl3) δ ppm=3.83 (s, 3 H), 6.92-7.03 (m, 3 H), 7.25-7.35 (m, 2 H), 7.39-7.50 (m, 2 H).

Workup

  1. waitThe reaction mixture turned green after −1 min
  2. stirringThe mixture was stirred at room temperature for 18 h after which time the reaction
  3. customwas quenched with water
  4. additiondiluted with DCM
  5. customThe organic layer was collected (phase separator)
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-20a3347109a541b0b323bdcb6d60aae4
Source dataset
uspto-grants-2016_04
Patent number
US09321746B2

Reaction notes

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