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

HRID 219977Notes

Reaction equation

HRID 219977 reaction equation
[CH3:1][O:2][CH2:3][C:4]1[CH:9]=[C:8]([C:10](O)=[O:11])[CH:7]=[CH:6][C:5]=1[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[CH3:19].C(Cl)(=O)C([Cl:23])=O.CN(C=O)C>C(Cl)Cl>[CH3:1][O:2][CH2:3][C:4]1[CH:9]=[C:8]([C:10]([Cl:23])=[O:11])[CH:7]=[CH:6][C:5]=1[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[CH3:19]

Participants

5

Reactant 3

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

Product 1

HCID 585540922-(Methoxymethyl)-2'-methylbiphenyl-4-carbonyl chloride

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of Intermediate 28 (2 g; 7.80 mmol) in DCM (40 mL) was added oxalyl chloride (1.98 mL; 23.41 mmol) followed by DMF (60 μL) under vigorous stirring at RT. After 2 h, solvents were removed under vacuum to give 2-(methoxymethyl)-2′-methylbiphenyl-4-carbonyl chloride as a yellow oil that was dried under vacuum. To a solution of Intermediate 62 (150 mg; 0.49 mmol) in CH3CN (1.50 mL) and DI EA (0.33 mL) was added a solution of 2-(methoxymethyl)-2′-methylbiphenyl-4-carbonyl chloride (134.07 mg; 0.49 mmol) in CH3CN (1.50 mL). Reaction mixture was stirred at RT for 1 h 30 after which it was heated to 150° C., 30 min under microwave irradiations. Reaction mixture was concentrated under vacuum, dissolved in DCM and purified by column chromatography (EtOAc:cHex from 10:90 to 80:20) to give the title compound as a colorless oil. LC/MS (Method B): 528.5 (M+H)+.

Workup

  1. customsolvents were removed under vacuum

Sources & evidence

ORD record
ord-c504092c717049bfab31d3e75f958f49
Source dataset
uspto-grants-2012_06
Patent number
US08202865B2

Reaction notes

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