Ammonium Chloride → 5-Bromo-2-chlorobenzaldehyde

HRID 909774Notes

Reaction equation

[H-].[H-].[H-].[H-].[Li+].[Al+3].[Br:7][C:8]1[CH:9]=[CH:10][C:11]([Cl:20])=[C:12]([CH:19]=1)[C:13](N(OC)C)=[O:14].[Cl-].[NH4+]>O1CCCC1>[Br:7][C:8]1[CH:9]=[CH:10][C:11]([Cl:20])=[C:12]([CH:19]=1)[CH:13]=[O:14]

Participants

Conditions

Temperature: -15 °C

Procedure

LiAlH4 (1.47 g, 0.0388 mol) was added little by little to a tetrahydrofuran (108 mL) solution of 5-bromo-2-chloro-N-methoxy-N-methylbenzamide (10.8 g, 0.0388 mol) so that the internal temperature did not exceed −10° C. The reaction mixture was stirred at −15° C. for one hour and carefully added with a saturated ammonium chloride aqueous solution and deposited insolubles were filtered off with celite. After the filtrate was extracted with ethyl acetate, the organic layer was washed with 1M hydrochloric acid, a saturated sodium bicarbonate aqueous solution, brine, and then dried with anhydrous magnesium sulfate. After the desiccant was filtered off, the solvent was evaporated under reduced pressure to obtain 5-bromo-2-chlorobenzaldehyde (8.1 g, 95%) as a pale yellow crystal. This was used in the next reaction without purification.

Workup

customdid not exceed −10° C
filtrationwere filtered off with celite
extractionAfter the filtrate was extracted with ethyl acetate
washthe organic layer was washed with 1M hydrochloric acid
dry with materiala saturated sodium bicarbonate aqueous solution, brine, and then dried with anhydrous magnesium sulfate
filtrationAfter the desiccant was filtered off
customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record: ord-f658e5e1362c4965aaea6ab3bc4d48fd
Source dataset: uspto-grants-2011_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08017792B2

Reaction notes

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