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

HRID 874499

Reaction equation

HRID 874499 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-010ece6468994f4184278acfaf9b07f0
Source dataset
uspto-grants-2015_03
Patent number
US08980890B2

Linked notes

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