N-bromobutanimide → Methyl 2-(2-bromothiophen-3-yl)acetate

HRID 1952497Notes

Reaction equation

HRID 1952497 reaction equation
[Br:1][C:2]1[S:3][C:4](C(=O)C2C=CC(I)=C([N+]([O-])=O)C=2)=[CH:5][C:6]=1[CH2:7][C:8]([O:10][CH3:11])=[O:9].C1C(=O)N(Br)C(=O)C1>C1COCC1>[Br:1][C:2]1[S:3][CH:4]=[CH:5][C:6]=1[CH2:7][C:8]([O:10][CH3:11])=[O:9]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 67496104Methyl 2-(2-bromo-5-(4-iodo-3-nitrobenzoyl)thiophen-3-yl)acetate

Product 1

HCID 57116941Methyl 2-(2-bromothiophen-3-yl)acetateYield 97%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of the above ester (10.00 g, 64.02 mmol) in THF (100 mL) was added NBS (11.40 g, 64.02 mmol). The resulting mixture was refluxed for two and a half hours. The solvent was removed in vacuo. MPLC purification (Hex:EtOAc/9:1) of the residue gave methyl 2-(2-bromothiophen-3-yl)acetate as a colorless oil (14.55 g, 97%). 1H NMR (400 MHz, CDCl3) δ 7.25 (d, J=5.6 Hz, 1H). 6.93 (d, J=5.6 Hz, 1H), 3.72 (s, 3H), and 3.64 (s, 2H).

Workup

  1. temperatureThe resulting mixture was refluxed for two and a half hours
  2. customThe solvent was removed in vacuo
  3. customMPLC purification (Hex:EtOAc/9:1) of the residue

Sources & evidence

ORD record
ord-3525815d24984e69ba95205d4f5f33b5
Source dataset
uspto-grants-2013_03
Patent number
US08404728B2

Reaction notes

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