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

HRID 714520

Reaction equation

HRID 714520 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-c684f8a700ae4cda99395bea95117d31
Source dataset
uspto-grants-2015_11
Patent number
US09187447B2

Linked notes

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