5-Bromosalicylic acid → (4-Fluorophenyl)methyl 5-bromo-2-{[(4-fluorophenyl)methyl]oxy}benzoate

HRID 1623707Notes

Reaction equation

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

Participants

Conditions

Temperature: 70 °C

Procedure

Neat 1-(bromomethyl)-4-fluorobenzene (1533 mg, 8.11 mmol) was added over 1 min to a stirred suspension of 5-bromo-2-hydroxybenzoic acid (800 mg, 3.69 mmol) and potassium carbonate (1274 mg, 9.22 mmol) in acetone (60 ml) in air at room temperature. The reaction mixture was stirred at 70° C. overnight. After filtering, the filtrate was evaporated to give a solid, which was dried in vacuo to yield the title compound as a white solid. 1.56 g.

Workup

filtrationAfter filtering
customthe filtrate was evaporated
customto give a solid, which
customwas dried in vacuo

Sources & evidence

ORD record: ord-ffd0ba8770d44e21a4a5374126998d79
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08778939B2

Reaction notes

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