Diethylamine → HCID 66730454, compound

HRID 2383702Notes

Reaction equation

[Br:1][C:2]1[CH:9]=[C:8]([F:10])[C:5]([CH:6]=O)=[C:4]([F:11])[CH:3]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[CH2:26]([NH:28][CH2:29][CH3:30])[CH3:27]>>[Br:1][C:2]1[CH:9]=[C:8]([F:10])[C:5]([CH2:6][N:28]([CH2:29][CH3:30])[CH2:26][CH3:27])=[C:4]([F:11])[CH:3]=1

Participants

Reactant 3

HCID 8021Diethylamine

HCID 27732904-Bromo-2,6-difluorobenzaldehyde

HCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 66730454HCID 66730454, compoundYield 86%

Procedure

According to procedure for the synthesis of Example A211A, by using 4-bromo-2,6-difluorobenzaldehyde (610 mg, 2.76 mmol), sodium triacetoxyborohydride (883.35 mg, 4.15 mmol) and diethylamine (425.21 mL, 4.15 mmol) to give the title compound as a colorless oil (660 mg, 86%). 1H NMR (400 MHz, CDCl3) δ 7.06 (d, J=6.4 Hz, 2H), 3.61 (s, 2H), 2.55-2.50 (m, 4H), 1.07 (t, J=6.8 Hz, 6H); MS ESI 279.9 [M+H]+, calcd for [C11H14BrF2N+H]+ 278.03.

Sources & evidence

ORD record: ord-7f3dc796fe4a4c0bbadcaaaa1ba769e8
Source dataset: uspto-grants-2012_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08263596B2

Reaction notes

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