Formic Acid → Formamide, N-(4-bromophenyl)-

HRID 1784419

Reaction equation

HRID 1784419 reaction equation
[CH:1]([OH:3])=O.C(OC(=O)C)(=O)C.[Br:11][C:12]1[CH:18]=[CH:17][C:15]([NH2:16])=[CH:14][CH:13]=1>C1COCC1>[Br:11][C:12]1[CH:18]=[CH:17][C:15]([NH:16][CH:1]=[O:3])=[CH:14][CH:13]=1

Participants

5

Reactant 3

HCID 284Formic AcidHCID 78074-BromoanilineHCID 7918Acetic Anhydride

Product 1

HCID 17474Formamide, N-(4-bromophenyl)-Yield 70.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Formic acid (7 mL, 186 mmol) and acetic anhydride (140.1 mL, 150 mmol) were heated together at 55° C. for 2 hours. The mixture was cooled to room temperature, THF (11 mL) was added followed by 4-bromoaniline (10 g, 58 mmol) in THF (20 mL). The mixture was stirred at room temperature for 3 hours before evaporating to dryness. Trituration of the solid gave the subtitled compound as a light brown solid (8.22 g). MH− 198/200. 1H NMR δ (CDCl3) 6.93-7.04 (2H, d), 7.24 (2H, s), 8.59-8.70 (1H, d).

Workup

  1. custombefore evaporating to dryness

Sources & evidence

ORD record
ord-e3d57e90e24f442b8a01474c6fd65590
Source dataset
uspto-grants-2009_03
Patent number
US07504392B2

Linked notes

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