Cesium carbonate → Methyl 4-cyano-3-(cyclobutyloxy)benzoate

HRID 906105Notes

Reaction equation

[C:1]([C:3]1[CH:12]=[CH:11][C:6]([C:7]([O:9][CH3:10])=[O:8])=[CH:5][C:4]=1[OH:13])#[N:2].C(=O)([O-])[O-].[Cs+].[Cs+].Br[CH:21]1[CH2:24][CH2:23][CH2:22]1>CN(C=O)C>[C:1]([C:3]1[CH:12]=[CH:11][C:6]([C:7]([O:9][CH3:10])=[O:8])=[CH:5][C:4]=1[O:13][CH:21]1[CH2:24][CH2:23][CH2:22]1)#[N:2]

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of methyl 4-cyano-3-hydroxybenzoate (0.067 g, 0.38 mmol) in 2 ml of DMF was added cesium carbonate (0.2 g, 0.62 mmol), bromocyclobutane (0.051 g, 0.38 mmol), and the reaction mixture was heated at 60° C. and stirred at this temperature for 3 hrs. The reaction mixture was cooled to RT, poured into ice water, and extracted several times with ethyl acetate (3×20 ml). The organic solution was dried over Na2SO4, filtered, rotary evaporated to dryness then dried in vacuo to provide methyl 4-cyano-3-(cyclobutyloxy)benzoate (0.055 g, 63%). 1H NMR (400 MHz, CD3OD): 7.74 (d, 1H), 7.67 (d, 1H), 7.54 (s, 1H), 3.93 (s, 3H), 2.57-2.52 (m, 2H), 2.26-2.21 (m, 2H), 1.94-1.90 (m, 1H), 1.94-1.78 (m, 2H). MS (EI) for C13H13NO3: 232 (MH+).

Workup

temperatureThe reaction mixture was cooled to RT
extractionextracted several times with ethyl acetate (3×20 ml)
dry with materialThe organic solution was dried over Na2SO4
filtrationfiltered
customrotary evaporated to dryness
customthen dried in vacuo

Sources & evidence

ORD record: ord-64d2f26b759a4ba79be87bd86518dede
Source dataset: uspto-grants-2011_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08012956B2

Reaction notes

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