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

HRID 69805Notes

Reaction equation

HRID 69805 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, 3 H), 8.01 (s, 1 H), 6.70 (s, 1 H), 4.08 (s, 1 H).

Workup

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

Sources & evidence

ORD record
ord-86c1c2f1fa90403ebe0f9457a566b5a0
Source dataset
uspto-grants-2014_09
Patent number
US08822511B2

Reaction notes

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