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

HRID 928955

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, 0.184 mol) was dispersed into a solution of 2,3,4-trifluorophenol (13.64 g, 0.092 mol) in acetone (300 mL). To the stirred suspension was added the solution of benzyl bromide (17.31 g, 101.21 mmol) in acetone (100 mL) dropwisely. The mixture was heated under reflux at 50° C. for 24 h, allowed to cool to room temperature, and filtered. The filter cake was washed with acetone (50 mL×3), and acetone was removed under reduced pressure. The residue was dissolved in ethyl acetate (500 mL). The solution was washed with 5% sodium hydroxide (50 mL), water (150 mL) and brine (150 mL) sequentially and dried over Na2SO4. The solvent was removed in vacuo to yield a pale yellow solid (19.89 g, 90% 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
temperatureto cool to room temperature
filtrationfiltered
washThe filter cake was washed with acetone (50 mL×3), and acetone
customwas removed under reduced pressure
dissolutionThe residue was dissolved in ethyl acetate (500 mL)
washThe solution was washed with 5% sodium hydroxide (50 mL), water (150 mL) and brine (150 mL) sequentially
dry with materialdried over Na2SO4
customThe solvent was removed in vacuo

Sources & evidence

ORD record: ord-6131eb85bf16441fadf990c4325637fa
Source dataset: uspto-grants-2016_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09290468B2

Linked notes

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