Water → Ethyl acetate hexane
Reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5](C2C=CC=C3C=2C=CC=[C:13]3[CH2:18][OH:19])=[CH:4][CH:3]=1.[CH:20]1(B(O)O)[CH2:22]C1.C1(C)C=CC=CC=1.[OH2:33]>CCOC(C)=O.CC([O-])=O.CC([O-])=O.[Pd+2].C1(P(C2CCCCC2)C2CCCCC2)CCCCC1>[CH3:20][CH2:22][O:33][C:18]([CH3:13])=[O:19].[CH3:6][CH2:7][CH2:2][CH2:3][CH2:4][CH3:5]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 3
Conditions
- Temperature
- 100 °C
Procedure
(5-(4-Bromophenyl)naphthalen-1-yl)methanol (130 mg), cyclopropylboronic acid (71 mg, 2 eq.), Pd(OAc)2 (5 mg, 0.05 eq.), tricyclohexylphosphine (12 mg, 0.1 eq.), and K2PO4 (308 mg, 3.5 eq.) were combined in a flask with 3 mL toluene and 1 mL H2O and degassed. Reaction mixture was then refluxed at 100° C. for 3 hours. Solution was cooled to room temperature then diluted with EtOAc and washed with saturated NaHCO3. The organic layer was dried over sodium sulfate and concentrated. Chromatography achieved using ISCO max gradient 35% EtOAc/hexane yielding product as a brown oil (86 mg, 75% yield). 1H NMR (400 MHz) (CDCl3) δ 8.17-8.15 (m, 1H), 7.96-7.94 (m, 1H), 7.61 (dd, J=8 Hz, J=8 Hz, 1H), 7.56-7.53 (m, 2H), 7.49-7.47 (m, 1H), 7.43-7.40 (m, 2H), 7.25-7.23 (m, 2H), 5.19 (s, 2H), 2.08-2.01 (m, 1H), 1.11-1.06 (m, 2H), 0.87-0.83 (m, 2H). 13C NMR (100 MHz) (CDCl3) δ143.16, 141.02, 138.03, 136.48, 132.17, 131.62, 130.13, 130.05, 138.27, 126.80, 125.84, 125.55, 125.36, 125.27, 123.00, 63.90, 15.28, 9.41.
Workup
- customdegassed
- customReaction mixture
- temperatureSolution was cooled to room temperature
- washwashed with saturated NaHCO3
- dry with materialThe organic layer was dried over sodium sulfate
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-c05c068396864273853294b578d7a5dd
- Source dataset
- uspto-grants-2015_08
- Patent number
- US09102617B2
Reaction notes
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