5-Bromosalicylic acid → HCID 67107238, compound

HRID 1623643Notes

Reaction equation

Br[CH2:2][C:3]1[CH:10]=[CH:9][C:6]([C:7]#[N:8])=[CH:5][CH:4]=1.[Br:11][C:12]1[CH:13]=[CH:14][C:15]([OH:21])=[C:16]([CH:20]=1)[C:17]([OH:19])=[O:18].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[Br:11][C:12]1[CH:13]=[CH:14][C:15]([O:21][CH2:2][C:3]2[CH:10]=[CH:9][C:6]([C:7]#[N:8])=[CH:5][CH:4]=2)=[C:16]([CH:20]=1)[C:17]([O:19][CH2:2][C:3]1[CH:10]=[CH:9][C:6]([C:7]#[N:8])=[CH:5][CH:4]=1)=[O:18]

Participants

Conditions

Temperature: 55 °C

Procedure

4-(Bromomethyl)benzonitrile (318 mg, 1.622 mmol) was added in a single charge to a stirred suspension of 5-bromo-2-hydroxybenzoic acid (160 mg, 0.74 mmol) and potassium carbonate (204 mg, 1.48 mmol) in acetone (40 ml) at 20° C. The reaction mixture was stirred at 55° C. for 18 h. The organic phase was evaporated and the residue was washed with water (25 ml), extracted with ethyl acetate (3×30 ml) and evaporated in vacuo to yield the title compound as an off-white solid. 300 mg.

Workup

customThe organic phase was evaporated
washthe residue was washed with water (25 ml)
extractionextracted with ethyl acetate (3×30 ml)
customevaporated in vacuo

Sources & evidence

ORD record: ord-6b631baa4a604273802511a1dad0d72d
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08778939B2

Reaction notes

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