(4-Bromo-3-fluorophenyl)(2,2-diethoxyethyl)sulfane → 5-Bromo-6-fluorobenzo[b]thiophene

HRID 923684Notes

Reaction equation

HRID 923684 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][CH2:9][CH:10](OCC)OCC)=[CH:4][C:3]=1[F:17]>ClC1C=CC=CC=1>[Br:1][C:2]1[CH:7]=[CH:6][C:5]2[S:8][CH:9]=[CH:10][C:4]=2[C:3]=1[F:17].[Br:1][C:2]1[C:3]([F:17])=[CH:4][C:5]2[S:8][CH:9]=[CH:10][C:6]=2[CH:7]=1

Participants

4

Reactant 1

HCID 90418081(4-Bromo-3-fluorophenyl)(2,2-diethoxyethyl)sulfane

Product 2

HCID 709824575-Bromo-6-fluorobenzo[b]thiopheneHCID 904173805-Bromo-4-fluorobenzo[b]thiophene

Reagents, catalysts & solvents 1

HCID 7964ChlorobenzeneSolvent2×

Conditions

Temperature
130 °C

Procedure

Polyphosphoric acid (13.9 g) was stirred in chlorobenzene (50 mL) at 130° C. (4-bromo-3-fluorophenyl)(2,2-diethoxyethyl)sulfane (7.7 g, 0.0238 mol) in chlorobenzene (15.4 mL) was added dropwise at 130° C. The mixture was then stirred at 130° C. for 10 h. The solvent was removed and the residue was extracted with toluene, hexane, and then water. The organic phase was combined and washed with saturated NaHCO3 solution and brine, and then dried over Na2SO4. The products 5-bromo-4-fluorobenzo[b]thiophene and 5-bromo-6-fluorobenzo[b]thiophene were obtained after purification via column chromatography (3.6 g, 65.5%).

Workup

  1. additionwas added dropwise at 130° C
  2. customThe solvent was removed
  3. extractionthe residue was extracted with toluene, hexane
  4. washwashed with saturated NaHCO3 solution and brine
  5. dry with materialdried over Na2SO4

Sources & evidence

ORD record
ord-825f7f27a45f489580dc85710ad4848a
Source dataset
uspto-grants-2016_03
Patent number
US09278985B2

Reaction notes

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