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

HRID 882966
Notes
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Reaction equation

HRID 882966 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]
ParticipantsProcedureSources & evidenceReaction notes

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 53249357Formaldehyde;rhodium;tris(triphenylphosphane)CatalystHCID 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-843b16ae77e44d478946b8a4599c9546
Source dataset
uspto-grants-2012_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08236799B2

Reaction notes

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On this pageParticipantsProcedureSources & evidenceReaction notes