Sodium hydride → HCID 68227568, compound

HRID 2368807Notes

Reaction equation

HRID 2368807 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]([OH:13])[C:9]([F:12])([F:11])[F:10])=[CH:4][CH:3]=1.[H-].[Na+].C[O:17][C:18]1[CH:25]=[CH:24][C:21]([CH2:22]Br)=[CH:20][CH:19]=1>C1COCC1.[I-].C([N+](CCCC)(CCCC)CCCC)CCC>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]([O:13][CH2:22][C:21]2[CH:24]=[CH:25][C:18]([OH:17])=[CH:19][CH:20]=2)[C:9]([F:11])([F:12])[F:10])=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 1650214-Methoxybenzyl bromideHCID 12640349(1R)-1-(4-Bromophenyl)-2,2,2-trifluoroethan-1-ol

Product 1

HCID 68227568HCID 68227568, compound

Reagents, catalysts & solvents 2

HCID 67553Tetrabutylammonium IodideCatalystHCID 8028TetrahydrofuranSolvent

Procedure

(R)-1-(4-bromophenyl)-2,2,2-trifluoroethanol (3.5 g, synthesis described in J. Org. Chem. 2009, 74, 1605-1610) was dissolved in THF (50 ml) under an argon atmosphere, NaH (719 mg) was added at 0° C. followed by tetrabutylammonium iodide (507 mg) then 4-methoxy-benzylbromide (3.04 g) and the mixture was stirred for 3.5 h at 20° C.

Sources & evidence

ORD record
ord-03dc4176a799479294e2c72abfd5d351
Source dataset
uspto-grants-2014_04
Patent number
US08703807B2

Reaction notes

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