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

HRID 2427455Notes

Reaction equation

HRID 2427455 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-194f609a09f74839a2fb9bc9ea0c0080
Source dataset
uspto-grants-2011_06
Patent number
US07968574B2

Reaction notes

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