Boron trifluoride etherate → Dibenz[b,e]oxepin-11(6H)-one

HRID 1946648

Reaction equation

[O:1]([CH2:8][C:9]1[CH:17]=[CH:16][CH:15]=[CH:14][C:10]=1[C:11]([OH:13])=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.FC(F)(F)C(OC(=O)C(F)(F)F)=O.B(F)(F)F.CCOCC>C(Cl)Cl>[CH:4]1[C:3]2[C:11](=[O:13])[C:10]3[CH:14]=[CH:15][CH:16]=[CH:17][C:9]=3[CH2:8][O:1][C:2]=2[CH:7]=[CH:6][CH:5]=1

Participants

Conditions

Temperature: 40 °C

Procedure

The 2-(phenoxymethyl)benzoic acid (22.18 g, 97 mmol) was dissolved in DCM (200 mL) and trifluoroacetic anhydride (20.59 mL, 146 mmol) was added, followed by a catalytic amount of borontrifluoride etherate (2.22 mL, 17.5 mmol). The reaction mixture was heated at 40° C. for 2 hours. The solution was then washed with water, sodium bicarbonate (saturated solution) and water. The organic phases was dried over sodium sulfate, filtered and concentrated under reduced pressure. The crude product was purified on silica gel (10-20% ethyl acetate in hexanes) to afford title compound 482 (19.937 g, 98%) as a light pink solid. MS (m/z): 211.1 (M+H).

Workup

washThe solution was then washed with water, sodium bicarbonate (saturated solution) and water
dry with materialThe organic phases was dried over sodium sulfate
filtrationfiltered
concentrationconcentrated under reduced pressure
customThe crude product was purified on silica gel (10-20% ethyl acetate in hexanes)

Sources & evidence

ORD record: ord-1a116199bdfc4aa1ba3fae8ed73bdf21
Source dataset: uspto-grants-2013_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08399452B2

Linked notes

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