Bromine → 3-Bromo-5-chlorobenzo[b]thiophene

HRID 1599591Notes

Reaction equation

HRID 1599591 reaction equation
[Br:1]Br.[Cl:3][C:4]1[CH:12]=[CH:11][C:7]2[S:8][CH:9]=[CH:10][C:6]=2[CH:5]=1>C(O)(=O)C>[Br:1][C:10]1[C:6]2[CH:5]=[C:4]([Cl:3])[CH:12]=[CH:11][C:7]=2[S:8][CH:9]=1

Participants

4

Reactant 2

HCID 24408BromineHCID 113097545-Chlorobenzo(b)thiophene

Product 1

HCID 142423383-Bromo-5-chlorobenzo[b]thiopheneYield 76.5%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Conditions

Temperature
50 °C

Procedure

A solution of bromine (0.31 g, 1.95 mmol) in 1.0 ml glacial acetic acid was added to a stirred solution of 5-chlorobenzo[b]thiophene (0.300 g, 1.77 mmol)in glacial acetic acid (1.0 ml) under nitrogen atmosphere. The reaction was heated to 50° C. for 4 hours, the volatiles removed under reduced pressure, the residue diluted in methylene chloride, washed with aq. sodium bicarbonate and with brine and dried over sodium sulfate. Evaporation gave 0.335 g (76%) of a tan solid. mp 85-86C., FDMS m/e=249 (M+2).

Workup

  1. customthe volatiles removed under reduced pressure
  2. additionthe residue diluted in methylene chloride
  3. washwashed with aq. sodium bicarbonate and with brine
  4. dry with materialdried over sodium sulfate
  5. customEvaporation

Sources & evidence

ORD record
ord-ad11acbb4df943789c069d3d7bbe649d
Source dataset
uspto-grants-1998_04
Patent number
US05741789

Reaction notes

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