4-Bromothiophene-2-carbaldehyde → HCID 76745063, compound

HRID 1951643Notes

Reaction equation

HRID 1951643 reaction equation
[CH3:1][O:2][C:3](=[O:8])[CH2:4][N:5]=[N+:6]=[N-:7].[Br:9][C:10]1[CH:11]=[C:12]([CH:15]=O)[S:13][CH:14]=1.C[O-].[Na+]>CO>[CH3:1][O:2][C:3](=[O:8])[C:4]([N:5]=[N+:6]=[N-:7])=[CH:15][C:12]1[S:13][CH:14]=[C:10]([Br:9])[CH:11]=1

Participants

5

Reactant 3

HCID 877924-Bromothiophene-2-carbaldehydeHCID 4020482Methyl 2-azidoacetateHCID 10942334Sodium Methoxide

Product 1

HCID 76745063HCID 76745063, compoundYield 71.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Conditions

Temperature
0 °C

Procedure

To a solution of azido-acetic acid methyl ester (25 g, 220 mmol) and 15 g of 4-bromo-thiophene-2-carbaldehyde (14.0 g, 73 mmol) in 50 ml of MeOH cooled at −25° C. was added a solution NaOMe in MeOH (51 ml, 4.36 M). The resulting mixture (slush) was stirred with a mechanical stirrer for 2 h at 0° C. and the 200 g of ice was added. The yellow solid was collected by filtration and air-dried to give 15 g of the title product which was used for the next step without further purification.

Workup

  1. filtrationThe yellow solid was collected by filtration
  2. customair-dried

Sources & evidence

ORD record
ord-b61ce7544a43401b96d841e828da878f
Source dataset
uspto-grants-2013_03
Patent number
US08404736B2

Reaction notes

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