Hydrochloric Acid → 4,5-Dichloro-2-fluorobenzaldehyde

HRID 1484180Notes

Reaction equation

[Cl:1][C:2]1[C:13]([Cl:14])=[CH:12][C:5]([C:6](N(OC)C)=[O:7])=[C:4]([F:15])[CH:3]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].Cl>C1COCC1.O>[Cl:1][C:2]1[C:13]([Cl:14])=[CH:12][C:5]([CH:6]=[O:7])=[C:4]([F:15])[CH:3]=1

Participants

Conditions

Temperature: 25 °C

Procedure

To a stirring solution of 4,5-dichloro-2-fluoro-N-methoxy-N-methyl-benzamide (5.1 g, 20.23 mmol) in THF (100 mL) at −78° was added a solution of lithium aluminum hydride in THF (12.14 mL of 2 M, 24.28 mmol). After 3 h at −78° C., 50 mL water was added followed by 50 mL of 1N HCl. The reaction was allowed to warm to 25° C. and stirred for 1 h. The reaction was diluted with water and extracted with diethyl ether. The ether was dried over Na2SO4, filtered, and concentrated to provide crude 4,5-dichloro-2-fluoro-benzaldehyde that was taken directly into the next step without further purification.

Workup

extractionextracted with diethyl ether
dry with materialThe ether was dried over Na2SO4
filtrationfiltered
concentrationconcentrated

Sources & evidence

ORD record: ord-2b7b421bb02c4d2abff3d56da062922a
Source dataset: uspto-grants-2016_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09421196B2

Reaction notes

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