Diethyl Ether → (R)-1-(1-(Benzyloxy)-3-fluoropropan-2-yl)-4-bromo-2-methylbenzene

HRID 708884Notes

Reaction equation

HRID 708884 reaction equation
CS(O[CH2:6][C@H:7]([C:17]1[CH:22]=[CH:21][C:20]([Br:23])=[CH:19][C:18]=1[CH3:24])[CH2:8][O:9][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)(=O)=O.CCCC[N+](CCCC)(CCCC)CCCC.[F-:42].C(OCC)C>CC(O)(C)C>[CH2:10]([O:9][CH2:8][C@@H:7]([C:17]1[CH:22]=[CH:21][C:20]([Br:23])=[CH:19][C:18]=1[CH3:24])[CH2:6][F:42])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 2724141Tetrabutylammonium FluorideHCID 118093144(R)-3-(Benzyloxy)-2-(4-bromo-2-methylphenyl)propyl methanesulfonate

Product 1

HCID 118092969(R)-1-(1-(Benzyloxy)-3-fluoropropan-2-yl)-4-bromo-2-methylbenzeneYield 76.2%

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Conditions

Temperature
80 °C

Procedure

To 24A (0.74 g, 1.790 mmol) in tBuOH (10 mL) was added TBAF (1.0 M in THF, 5.37 mL, 5.37 mmol). The mixture was stirred at 80° C. for 2 h. Ethyl ether was added and the mixture was filtered. The filtrate was evaporated and the crude product was purified by flash chromatography (0-30% EtOAc/hexanes) to give 24B (0.46 g, 1.364 mmol, 76% yield) as colorless oil. 1H NMR (400 MHz, chloroform-d) δ ppm 7.27-7.43 (m, 7H) 7.13 (d, J=8.34 Hz, 1H) 4.74 (d, J=5.56 Hz, 1H) 4.62 (d, J=5.56 Hz, 1H) 4.47-4.59 (m, 2H) 3.71-3.81 (m, 1H) 3.60-3.70 (m, 1H) 3.37-3.57 (m, 1H) 2.33 (s, 3H); 19F NMR (376 MHz, chloroform-d) δ ppm −224.19 (s, 1F).

Workup

  1. filtrationthe mixture was filtered
  2. customThe filtrate was evaporated
  3. customthe crude product was purified by flash chromatography (0-30% EtOAc/hexanes)

Sources & evidence

ORD record
ord-23c3f1bffd084c98956bb361e4131e71
Source dataset
uspto-grants-2015_11
Patent number
US09174974B2

Reaction notes

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