Ethyl Acetate → HCID 57891910, compound

HRID 1820692Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([O:8]C)=[CH:4][C:3]=1[O:10][C:11]1[CH:16]=[CH:15][C:14]([F:17])=[CH:13][CH:12]=1.B(Br)(Br)Br.CCCCCCC.C(OCC)(=O)C>C(Cl)Cl>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][C:3]=1[O:10][C:11]1[CH:16]=[CH:15][C:14]([F:17])=[CH:13][CH:12]=1

Participants

Conditions

Temperature: -78 °C

Procedure

Elution with 10:90 ethyl acetate:heptane with a gradient to 30:70 ethyl acetate:heptane afforded 1-chloro-2-(4-fluorophenoxy)-4-methoxybenzene (112 mg, 0.44 mmol, 49%). 1-Chloro-2-(4-fluorophenoxy)-4-methoxybenzene (110 mg, 0.44 mmol) prepared above, was dissolved in DCM (5.00 mL) and stirred under argon at −78° C. Boron tribromide (1.0M in DCM, 2.20 mL) was then added and the reaction stirred at −78° C. for 1 h. The reaction was allowed to warm to ambient temperature overnight, quenched with saturated Na2CO3 (aq) and then the aqueous and organic layers were separated. The solvent was removed in vacuo and the crude product was purified by chromatography on silica gel. Elution with 2:98 ethyl acetate:heptane with a gradient to 20:80 ethyl acetate:heptane afforded 4-chloro-3-(4-fluorophenoxy)phenol (92 mg, 0.38 mmol, 87%). M.S. (ESI) (m/z): 237, 239 [M−H]−

Workup

stirringthe reaction stirred at −78° C. for 1 h
temperatureto warm to ambient temperature overnight
customquenched with saturated Na2CO3 (aq)
customthe aqueous and organic layers were separated
customThe solvent was removed in vacuo
customthe crude product was purified by chromatography on silica gel
washElution with 2:98 ethyl acetate

Sources & evidence

ORD record: ord-5a1a2db3124c43a39657f6e9a770a1d9
Source dataset: uspto-grants-2009_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07605170B2

Reaction notes

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