Diphenylsilane → 4-(4-Bromo-3-fluorobenzyl)morpholine

HRID 1674757

Reaction equation

HRID 1674757 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([N:10]2[CH2:15][CH2:14][O:13][CH2:12][CH2:11]2)=O)=[CH:4][C:3]=1[F:16].C1([SiH2]C2C=CC=CC=2)C=CC=CC=1>C1COCC1.C=O.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[Rh]>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][N:10]2[CH2:11][CH2:12][O:13][CH2:14][CH2:15]2)=[CH:4][C:3]=1[F:16]

Participants

5

Reactant 2

HCID 69888DiphenylsilaneHCID 48474115(4-Bromo-3-fluorophenyl)(morpholin-4-yl)methanone

Product 1

HCID 534178184-(4-Bromo-3-fluorobenzyl)morpholine

Reagents, catalysts & solvents 2

HCID 53249357Carbonyltris(triphenylphosphine)rhodium(I)hydrideCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A 250 ml flask was charged with (4-bromo-3-fluorophenyl)(morpholino)methanone (4.569 g, 15.86 mmol) and dissolved in 16 mL of THF. Diphenylsilane (6.2 ml, 33.4 mmol) was added followed by carbonyltris(triphenylphosphine)rhodium(I)hydride (100 mg, 0.109 mmol) and the reaction stirred at room temperature for 20 hours.

Sources & evidence

ORD record
ord-23c3962c9eca4df782110f17247574e1
Source dataset
uspto-grants-2011_08
Patent number
US08003641B2

Linked notes

Loading…