5-Bromosalicylic acid → HCID 67107390, compound

HRID 1623645Notes

Reaction equation

[C:1]([C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][CH:10]=1)[CH2:6]Br)#[N:2].[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][CH2:6][C:5]2[CH:8]=[CH:9][CH:10]=[C:3]([C:1]#[N:2])[CH:4]=2)=[C:16]([CH:20]=1)[C:17]([O:19][CH2:6][C:5]1[CH:8]=[CH:9][CH:10]=[C:3]([C:1]#[N:2])[CH:4]=1)=[O:18]

Participants

Conditions

Temperature: 56 °C

Procedure

3-Cyanobenzylbromide (542 mg, 2.76 mmol) was added dropwise to a stirred suspension of 5-bromo-2-hydroxybenzoic acid (200 mg, 0.92 mmol) and potassium carbonate (255 mg, 1.84 mmol) in acetone (40 ml) over 1 min. The reaction mixture was then stirred at 56° C. for 24 h. The organic phase was evaporated and the residue was washed with water (25 ml), extracted with ethyl acetate (100 ml) and evaporated in vacuo to yield the title compound as an off white solid. 411 mg.

Workup

customThe organic phase was evaporated
washthe residue was washed with water (25 ml)
extractionextracted with ethyl acetate (100 ml)
customevaporated in vacuo

Sources & evidence

ORD record: ord-090de54aa420401aab8f3bba76c8f07d
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08778939B2

Reaction notes

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