2-Bromothiophene → HCID 19046237, compound

HRID 1781299Notes

Reaction equation

HRID 1781299 reaction equation
[F:1][C:2]1[CH:15]=[CH:14][CH:13]=[C:12]([F:16])[C:3]=1[C:4]([NH:6][CH:7](O)[C:8]([OH:10])=[O:9])=[O:5].[Br:17][C:18]1[S:19][CH:20]=[CH:21][CH:22]=1>CS(O)(=O)=O>[Br:17][C:18]1[S:19][C:20]([CH:7]([NH:6][C:4](=[O:5])[C:3]2[C:2]([F:1])=[CH:15][CH:14]=[CH:13][C:12]=2[F:16])[C:8]([OH:10])=[O:9])=[CH:21][CH:22]=1

Participants

4

Reactant 2

HCID 138512-BromothiopheneHCID 18472029HCID 18472029, compound

Product 1

HCID 19046237HCID 19046237, compoundYield 52.3%

Reagents, catalysts & solvents 1

HCID 6395Methanesulfonic AcidSolvent

Procedure

A solution of 4.76 g (20.6 mmol) of the product of Step A in 140 mL of methanesulfonic acid was immersed in an ice-water bath (temperature between 5°-10° C.). Then, 4.0 g (24.6 mmol) of 2-bromothiophene was added dropwise. It was stirred at the same temperature until a deep blue-black color formed. It was poured into ice-water and the resulting precipitate was filtered. The solid was triturated with methylene chloride to give 4.05 g of a tan solid: mp 198°-199° C. (dec.). 1H-NMR (DMSO-d6) δ9.80 (d,1H), 7.55 (m, 1H), 7.20 (m,3H), 7.00 (d, 1H), 5.80 (d, 1H).

Workup

  1. custom(temperature between 5°-10° C.)
  2. customformed
  3. filtrationthe resulting precipitate was filtered
  4. customThe solid was triturated with methylene chloride

Sources & evidence

ORD record
ord-5979ac0adc0b4a1b9ea3a8531e33ee0d
Source dataset
uspto-grants-1997_05
Patent number
US05633271

Reaction notes

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