Cesium carbonate → HCID 178445718, compound

HRID 2404081Notes

Reaction equation

[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7]([OH:12])[CH:6]=[CH:5]2.C(=O)([O-])[O-].[Cs+].[Cs+].CS(O[C@H:24]1[CH2:29][CH2:28][C@H:27]([C:30]([CH3:33])([CH3:32])[CH3:31])[CH2:26][CH2:25]1)(=O)=O>C(O)(C)(C)C.CC(=O)CC>[Br:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([O:12][C@H:24]3[CH2:29][CH2:28][C@H:27]([C:30]([CH3:33])([CH3:32])[CH3:31])[CH2:26][CH2:25]3)[CH:8]=2)[CH:3]=1

Participants

Conditions

Temperature: 110 °C

Procedure

6-bromonaphthalen-2-ol (CAS no. 15231-91-1) (3.0 g, 14.8 mmol, 1.0 eq.) was dissolved in a mixture of t-butanol/2-butanone (4 mL/2 mL). Then cesium carbonate (12 g, 37.2 mmol, 2.5 eq.) was added to the mixture and the mixture was stirred at 110° C. for 10 min. Then trans-4-tert-butylcyclohexyl methanesulfonate (3.48 g, 16.2 mmol, 1.1 eq.) was added to the mixture. The suspension was stirred at 110° C. under a nitrogen atmosphere for 15 h. The reaction mixture was extracted with ethyl acetate and the organic layer was purified by silica gel column chromatography using petroleum ether as eluent to give 2-bromo-6-(trans-4-tert-butylcyclohexyloxy)naphthalene as a slight yellow solid (1.7 g, yield: 32%). ESI-MS: 361.0 (M+H)+. 1H NMR (400 MHz, CDCl3) δ 7.89 (s, 1H), 7.63 (d, 1H), 7.56 (d, 1H), 7.47 (d, 1H), 7.15-7.11 (m, 2H), 4.26-4.24 (m, 1H), 2.27-2.25 (m, 2H), 1.89-1.87 (m, 2H), 1.45-1.09 (m, 5H), 0.89 (s, 9H).

Workup

stirringThe suspension was stirred at 110° C. under a nitrogen atmosphere for 15 h
extractionThe reaction mixture was extracted with ethyl acetate
customthe organic layer was purified by silica gel column chromatography

Sources & evidence

ORD record: ord-2ec933a904be412cbcc526d5e642d365
Source dataset: uspto-grants-2014_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08802659B2

Reaction notes

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