Benzyl Bromide → 1-(Benzyloxy)-2,3,4-trifluorobenzene

HRID 928946

Reaction equation

C(=O)([O-])[O-].[Na+].[Na+].[F:7][C:8]1[C:13]([F:14])=[C:12]([F:15])[CH:11]=[CH:10][C:9]=1[OH:16].[CH2:17](Br)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>CC(C)=O>[CH2:17]([O:16][C:9]1[CH:10]=[CH:11][C:12]([F:15])=[C:13]([F:14])[C:8]=1[F:7])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

Conditions

Temperature: 50 °C

Procedure

Sodium carbonate (19.50 g, 183.96 mmol) was dispersed into a solution of 2,3,4-trifluorophenol (13.64 g, 92.10 mmol) in acetone (300 mL). To the stirred suspension was added benzyl bromide (17.31 g, 101.21 mmol) dropwisely. The mixture was heated under reflux at 50° C. for 24 h. The acetone was removed under reduced pressure and the residue was dissolved in water (300 mL). The solution was extracted with ethyl acetate (100 mL×2). The combined organic extracts were washed with 5% sodium hydroxide (100 mL) and brine (100 mL) sequentially and dried over Na2SO4. The solvent was removed in vacuo to yield a pale yellow solid (19.89 g, 90.7% yield). 1H NMR (400 MHz, CDCl3): δ 7.40 (m, 5H), 6.85 (m, 1H), 6.64 (m, 1H), 5.15 (s, 2H).

Workup

temperatureThe mixture was heated
customThe acetone was removed under reduced pressure
dissolutionthe residue was dissolved in water (300 mL)
extractionThe solution was extracted with ethyl acetate (100 mL×2)
washThe combined organic extracts were washed with 5% sodium hydroxide (100 mL) and brine (100 mL) sequentially
dry with materialdried over Na2SO4
customThe solvent was removed in vacuo

Sources & evidence

ORD record: ord-02b6d58abe6a43db8f199e07bb9a2740
Source dataset: uspto-grants-2016_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09290468B2

Linked notes

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