Acetic Acid → 5-Bromothiophene-3-carboxylic acid

HRID 915690Notes

Reaction equation

HRID 915690 reaction equation
[CH:1]1[CH:2]=[C:3](C(O)=O)[S:4][CH:5]=1.[Br:9]Br.C[C:12]([OH:14])=[O:13]>>[Br:9][C:3]1[S:4][CH:5]=[C:1]([C:12]([OH:14])=[O:13])[CH:2]=1

Participants

4

Reactant 3

HCID 176Acetic Acid2×HCID 107002-Thiophenecarboxylic acidHCID 24408Bromine

Product 1

HCID 120399785-Bromothiophene-3-carboxylic acid

Procedure

Prepare a solution of thiophene carboxylic acid (500 mg, 3.90 mmol) in HOAc (5 mL). Add Br2 (0.17 mL, 0.85 mmol), in HOAc (3 mL), dropwise. Then stir the mixture for 15 minutes at room temperature under nitrogen. Quench the reaction with ice cold water and stir for an additional 10 minutes. Cool the solution −10° C. when the product will precipitate out. Filter the solution, rinse the filter cake with ice cold water, and dry the product to afford 473 mg of 5-bromothiophene-3-carboxylic acid as a white solid. 1H NMR (dimethylsulfoxide-d6) δ 12.90 (br s, 1H), 8.18 (d, J=1.5 Hz, 1H), 7.46 (d, J=1.5 Hz, 1H).

Workup

  1. customQuench
  2. customthe reaction with ice cold water
  3. stirringstir for an additional 10 minutes
  4. temperatureCool the solution −10° C. when the product
  5. customwill precipitate out
  6. filtrationFilter the solution
  7. washrinse the filter cake with ice cold water
  8. customdry the product

Sources & evidence

ORD record
ord-822bdef41d8d4d7c836ecb9b70ae52eb
Source dataset
uspto-grants-2007_09
Patent number
US07265246B2

Reaction notes

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