Bromoform → HCID 57704807, compound

HRID 2093195Notes

Reaction equation

HRID 2093195 reaction equation
N[C:2]1[CH:3]=[C:4]([C:9]2[CH:14]=[CH:13][C:12]([C:15]([O:17][CH3:18])=[O:16])=[CH:11][C:10]=2[CH3:19])[CH:5]=[CH:6][C:7]=1[Cl:8].N(OC(C)(C)C)=O.C(Br)(Br)[Br:28]>ClCCl>[Br:28][C:2]1[CH:3]=[C:4]([C:9]2[CH:14]=[CH:13][C:12]([C:15]([O:17][CH3:18])=[O:16])=[CH:11][C:10]=2[CH3:19])[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

5

Reactant 3

HCID 5558BromoformHCID 10906Tert-Butyl nitriteHCID 57704763Methyl 3'-amino-4'-chloro-2-methylbiphenyl-4-carboxylate

Product 1

HCID 57704807HCID 57704807, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
80 °C

Procedure

Methyl 3′-amino-4′-chloro-2-methylbiphenyl-4-carboxylate (946 mg, 3.43 mmol) was dissolved in a mixture of CHBr3 (5 mL) and dichloromethane (5 mL). To the above stirred mixture was added t-butyl nitrite (680 μL, 530.6 mg, 5.145 mmol). The reaction mixture was heated to 80° C. for 30 minutes. Aliquot (LCMS) indicated complete consumption of starting material. Crude mixture was purified by flash chromatography (SiO2, Biotage 40+S cartridge) to afford methyl 3′-bromo-4′-chloro-2-methylbiphenyl-4-carboxylate. LCMS calc.=339.97; found=340.98 (M+1)+.

Workup

  1. customconsumption of starting material
  2. customCrude mixture was purified by flash chromatography (SiO2, Biotage 40+S cartridge)

Sources & evidence

ORD record
ord-7bef1d42cec04045bb427a0b373ce3ff
Source dataset
uspto-grants-2013_05
Patent number
US08440702B2

Reaction notes

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