Trifluoroacetic acid → 1-(4-Bromo-2-furyl)methanamine trifluoroacetate

HRID 881182Notes

Reaction equation

HRID 881182 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH2:7][NH:8]C(=O)OC(C)(C)C)[O:5][CH:6]=1.[F:16][C:17]([F:22])([F:21])[C:18]([OH:20])=[O:19]>ClCCl>[F:16][C:17]([F:22])([F:21])[C:18]([OH:20])=[O:19].[Br:1][C:2]1[CH:3]=[C:4]([CH2:7][NH2:8])[O:5][CH:6]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 59148344HCID 59148344, compound

Product 1

HCID 666060541-(4-Bromo-2-furyl)methanamine trifluoroacetateYield 81%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Under a nitrogen atmosphere, a solution of tert-butyl [(4-bromo-2-furyl)methyl]carbamate (15.3 g, 55.4 mmol) in dichloromethane (86 mL) at 0° C. was treated with trifluoroacetic acid (43 mL) over 15 minutes. The reaction mixture warmed to room temperature over 30 minutes. The solvent was removed in vacuo and chased with toluene (3×50 mL). The product was lyophilized for 18 hours to give the desired product as a brown solid (13.0 g, 81%). LCMS calculated for C5H4BrO (M-NH2)+: m/z=158.9, 160.9. 1H NMR (400 MHz, DMSO-d6): δ 8.34 (br s, 3H), 8.01 (s, 1H), 6.70 (s, 1H), 4.08 (s, 1H).

Workup

  1. customThe solvent was removed in vacuo and chased with toluene (3×50 mL)

Sources & evidence

ORD record
ord-4ea4c6e50f0e421e8dedd92014484eff
Source dataset
uspto-grants-2015_03
Patent number
US08993605B2

Reaction notes

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