Dimethylformamide → 2-(Methoxymethyl)-2'-methylbiphenyl-4-carbonyl chloride

HRID 1630978Notes

Reaction equation

HRID 1630978 reaction equation
[C:1](Cl)(=O)[C:2]([Cl:4])=[O:3].CN(C=O)C.[CH3:12][O:13][CH2:14][C:15]1[CH:20]=C(C(O)=O)[CH:18]=[CH:17][C:16]=1[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=1[CH3:30]>C(Cl)Cl>[CH3:12][O:13][CH2:14][C:15]1[CH:20]=[C:1]([C:2]([Cl:4])=[O:3])[CH:18]=[CH:17][C:16]=1[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=1[CH3:30]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 594958222-(Methoxymethyl)-2'-methylbiphenyl-4-carboxylic acid

Product 1

HCID 585540922-(Methoxymethyl)-2'-methylbiphenyl-4-carbonyl chlorideYield 98%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Oxalyl chloride (2.0 mL, 23.6 mmol) and anhydrous DMF (0.060 mL, 0.78 mmol) were added into a solution of 2-(methoxymethyl)-2′-methylbiphenyl-4-carboxylic acid (2.0 g, 7.8 mmol) in anhydrous DCM (40 mL). After 15 hours at RT, the reaction mixture was concentrated under reduced pressure to give the title compound as a yellow oil (2.1 g, quantitative), which was used without further purification.

Workup

  1. concentrationthe reaction mixture was concentrated under reduced pressure

Sources & evidence

ORD record
ord-93107ee751f74b1db7021759035c9cb8
Source dataset
uspto-grants-2014_07
Patent number
US08791142B2

Reaction notes

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