Benzoyl chloride → HCID 53211784, compound

HRID 522509Notes

Reaction equation

[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[N+:9]([O-:11])=[O:10].[Li+].[Cl-].C([Cu])#N.[C:17](Cl)(=[O:24])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.[NH4+].[Cl-]>C1COCC1>[F:1][C:2]1[C:3]([N+:9]([O-:11])=[O:10])=[CH:4][CH:5]=[C:6]([F:8])[C:7]=1[C:17]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)=[O:24]

Participants

Conditions

Temperature: 25 °C

Procedure

2,4-Difluoro-1-nitrobenzene 15 (159 mg, 1.0 mmol) in THF (2 mL) was added to a solution of TMPZnCl.LiCl (2) (1.3 M in THF, 0.85 mL, 1.1 mmol) at 25° C. and the reaction mixture was then stirred at this temperature for 45 min according to TP 2. CuCN.2LiCl (1.0 M solution in THF, 1.1 mL, 1.1 mmol) was slowly added at −40 ° C. and the reaction mixture was stirred at the same temperature for 30 min. Then, benzoyl chloride (281 mg, 2.0 mmol) was added dropwise at −40° C. and the resulting mixture was allowed to warm up slowly to 25° C. overnight. The reaction mixture was then quenchend with a sat. aq. NH4Cl solution (20 mL), extracted with diethyl ether (3×50 mL) and dried over anhydrous Na2SO4. After filtration, the solvent was evaporated in vacuo. Purification by flash-chromatography (CH2Cl2/n-pentane, 1:2) furnished compound 17b (221 mg, 84%) as a colourless solid.

Workup

extractionextracted with diethyl ether (3×50 mL)
dry with materialdried over anhydrous Na2SO4
filtrationAfter filtration
customthe solvent was evaporated in vacuo
customPurification by flash-chromatography (CH2Cl2/n-pentane, 1:2)

Sources & evidence

ORD record: ord-f1eee90fe0654072b9e7710626b5ac0b
Source dataset: uspto-grants-2016_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09334237B2

Reaction notes

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