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

HRID 1907928

Reaction equation

HRID 1907928 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-7f048c54528c4de8b280552f6360c4a3
Source dataset
uspto-grants-2013_12
Patent number
US08598169B2

Linked notes

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