Toluene → Methyl 3,5-dicyclopropyl-4-(trifluoromethoxy)benzoate

HRID 402828

Reaction equation

Br[C:2]1[CH:3]=[C:4]([CH:9]=[C:10](Br)[C:11]=1[O:12][C:13]([F:16])([F:15])[F:14])[C:5]([O:7][CH3:8])=[O:6].C([O-])([O-])=O.[Cs+].[Cs+].[CH:24]1([B-](F)(F)F)[CH2:26][CH2:25]1.[K+].[C:32]1([CH3:38])C=CC=C[CH:33]=1>O.CC([O-])=O.CC([O-])=O.[Pd+2].C12(P(C34CC5CC(CC(C5)C3)C4)CCCC)CC3CC(CC(C3)C1)C2>[CH:24]1([C:2]2[CH:3]=[C:4]([CH:9]=[C:10]([CH:38]3[CH2:32][CH2:33]3)[C:11]=2[O:12][C:13]([F:16])([F:15])[F:14])[C:5]([O:7][CH3:8])=[O:6])[CH2:26][CH2:25]1

Participants

Conditions

Temperature: 100 °C

Procedure

To methyl 3,5-dibromo-4-(trifluoromethoxy)benzoate (500 mg, 1.32 mmol), Cs2CO3 (2586 mg, 7.94 mmol), Pd(OAc)2 (11.9 mg, 0.053 mmol), potassium cyclopropyltrifluoroborate (470 mg, 3.18 mmol) and di(1-adamantyl)-n-butylphosphine (28.5 mg, 0.079 mmol) was added toluene (12 mL) and water (1.2 mL). The reaction mixture was heated to 100° C. overnight. The reaction mixture was cooled to room temperature, diluted with water, extracted with DCM and evaporated in vacuo. The residue was purified by silica gel chromatography (0-20% EtOAc/hexanes) to yield the title compound (259 mg).

Workup

temperatureThe reaction mixture was cooled to room temperature
extractionextracted with DCM
customevaporated in vacuo
customThe residue was purified by silica gel chromatography (0-20% EtOAc/hexanes)

Sources & evidence

ORD record: ord-7fd07df0264a410eac9a56bdedf98093
Source dataset: uspto-grants-2014_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08742110B2

Linked notes

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