Water → Methyl 2-(4-bromothiophen-2-yl)acetate

HRID 410037

Reaction equation

HRID 410037 reaction equation
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH2:6][C:7]([O:9][CH3:10])=[O:8].[Al+3].[Cl-].[Cl-].[Cl-].[Br:15]Br.O>C(Cl)(Cl)Cl>[Br:15][C:4]1[CH:3]=[C:2]([CH2:6][C:7]([O:9][CH3:10])=[O:8])[S:1][CH:5]=1

Participants

6

Reactant 4

HCID 962WaterHCID 24408BromineHCID 88055Methyl thiophen-2-acetateHCID 6451240Aluminum(III) Chloride

Product 1

HCID 67367159Methyl 2-(4-bromothiophen-2-yl)acetateYield 41.2%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a solution of methyl 2-(thiophen-2-yl)acetate (5 g, 32 m mol) and anhydrous AlCl3 (10.7 g, 80 mmol) in CHCl3 (50 ml) was added dropwise bromine (1.8 ml, 34 mmol) at 0-5° C. over 30 min. When the addition was complete, the mixture was allowed to warm to room temperature overnight. Then it was poured into icy water (50 ml), extracted with EtOAc (30 ml×3). The combined organic phase was dried over Na2SO4, filtered and concentrated. Purification by column chromatography (PE/EtOAc=10/1) gave the product (3.1 g, 41%) as light yellow oil.

Workup

  1. additionWhen the addition
  2. extractionextracted with EtOAc (30 ml×3)
  3. dry with materialThe combined organic phase was dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customPurification by column chromatography (PE/EtOAc=10/1)

Sources & evidence

ORD record
ord-3d80e05f50c843e9ae83b5f4e55f3760
Source dataset
uspto-grants-2014_06
Patent number
US08759548B2

Linked notes

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