Dichloromethane → Ethyl 5-(bromomethyl)-2-(trifluoromethyl)furan-3-carboxylate

HRID 237249Notes

Reaction equation

HRID 237249 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[CH:10]=[C:9]([CH3:11])[O:8][C:7]=1[C:12]([F:15])([F:14])[F:13])=[O:5])[CH3:2].[Br:16]N1C(=O)CCC1=O.C(Cl)Cl.C([O-])(O)=O.[Na+]>C(Cl)(Cl)(Cl)Cl.CC(N=NC(C#N)(C)C)(C#N)C>[CH2:1]([O:3][C:4]([C:6]1[CH:10]=[C:9]([CH2:11][Br:16])[O:8][C:7]=1[C:12]([F:15])([F:13])[F:14])=[O:5])[CH3:2]

Participants

7

Reactant 4

HCID 6344DichloromethaneHCID 67184N-bromobutanimideHCID 516892Sodium BicarbonateHCID 2737208Ethyl 5-methyl-2-(trifluoromethyl)furan-3-carboxylate

Product 1

HCID 13237850Ethyl 5-(bromomethyl)-2-(trifluoromethyl)furan-3-carboxylateYield 38%

Reagents, catalysts & solvents 2

HCID 6547AzobisisobutyronitrileCatalystHCID 5943Carbon TetrachlorideSolvent

Procedure

To a solution of 5-methyl-2-trifluoromethyl-furan-3-carboxylic acid ethyl ester (0.95 g, 4.5 mmol) in CCl4 (12 mL) was added N-bromosuccinimide (0.84 g, 4.8 mmol) followed by AIBN (0.004 g, 0.01 mmol). After refluxing for 2 h, analytical HPLC analysis confirmed the reaction was complete. The reaction was cooled to rt, then CH2Cl2 and sat'd NaHCO3 (aq.) were added. The organic portion was separated and dried to provide the crude residue as a yellow oil. This material was purified by RP HPLC to provide the title compound (510 mg, 38%). MS (ESI): mass calcd. for C9H8BrF3O3, 300.0; m/z found, 302.9 [M+H]+. 1H NMR (CDCl3): 6.84 (s, 1H), 4.44 (s, 2H), 4.34 (q, J=7.2 Hz, 2H), 1.36 (t, J=7.1 Hz, 3H).

Workup

  1. temperatureAfter refluxing for 2 h
  2. customThe organic portion was separated
  3. customdried
  4. customto provide the crude residue as a yellow oil
  5. customThis material was purified by RP HPLC

Sources & evidence

ORD record
ord-50a405bed03c4c52a484f67738a091c4
Source dataset
uspto-grants-2014_02
Patent number
US08642583B2

Reaction notes

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