4-Hydroxybenzaldehyde → HCID 118113224, compound

HRID 1485100Notes

Reaction equation

OC1C=CC(C=O)=CC=1.BrC1CC1.[F:14][C:15]([F:24])([F:23])[C:16]1[N:21]=[CH:20][C:19]([OH:22])=[CH:18][CH:17]=1.[C:25]([C:27]1[CH:34]=[CH:33][C:30]([CH2:31]Br)=[CH:29][CH:28]=1)#[N:26]>>[F:24][C:15]([F:14])([F:23])[C:16]1[N:21]=[CH:20][C:19]([O:22][CH2:31][C:30]2[CH:33]=[CH:34][C:27]([C:25]#[N:26])=[CH:28][CH:29]=2)=[CH:18][CH:17]=1

Participants

Reactant 4

HCID 1264-Hydroxybenzaldehyde

HCID 78037Bromocyclopropane

HCID 869964-(Bromomethyl)benzonitrile

HCID 27833885-Hydroxy-2-(trifluoromethyl)pyridine

Product 1

HCID 118113224HCID 118113224, compoundYield 96.7%

Procedure

Instead of 4-hydroxybenzaldehyde and bromocyclopropane, 6-(trifluoromethyl)pyridin-3-ol (1.21 g) and 4-cyanobenzylbromide (1.45 g) were respectively used and treated by the same technique as in Reference Example 10-1 to give 4-({[6-(trifluoromethyl)pyridin-3-yl]oxy}methyl)benzonitrile as a pale brown solid (1.99 g).

Workup

additiontreated by the same technique as in Reference Example 10-1

Sources & evidence

ORD record: ord-79f3caaa09b4459ea6cc86983b613a99
Source dataset: uspto-grants-2016_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09422240B2

Reaction notes

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