t-Butyl bromide → 5-Tert-butylthiophene-2-carboxylic acid

HRID 235085Notes

Reaction equation

HRID 235085 reaction equation
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]([OH:8])=[O:7].[C:9](Br)([CH3:12])([CH3:11])[CH3:10]>C(Cl)Cl>[CH3:10][C:9]([C:5]1[S:1][C:2]([C:6]([OH:8])=[O:7])=[CH:3][CH:4]=1)([CH3:12])[CH3:11]

Participants

4

Reactant 2

HCID 10485t-Butyl bromideHCID 107002-Thiophenecarboxylic acid

Product 1

HCID 4583495-Tert-butylthiophene-2-carboxylic acidYield 46.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 5.0 g (39.02 mmol) of thiophene-2-carboxylic acid (Aldrich Chemical Co.) in 100 mL of methylene chloride stirred at 0° C. was added 11 g (82.5 mmol) of AICl3 and 5.8 g (43.0 mmol) of t-butyl bromide. The solution was stirred at room temperature for 18 hours then poured into 100 mL of ice water, and the mixture was extracted with ether. The extracts were washed with brine and dried over MgSO4, then concentrated to give 3.33 g of the title product. MS (M+H)+ : 202. NMR (CDCl3) δ:1.42 (s, 9H), 6.89 (d, 1H, J=4 Hz), 7.72 (d, 1H, J=4 Hz).

Workup

  1. extractionthe mixture was extracted with ether
  2. washThe extracts were washed with brine
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-50183175bd994b62ad3037b69ae3b2c7
Source dataset
uspto-grants-1997_01
Patent number
US05597832

Reaction notes

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