Borane → 3-[N-phenyl-N-(4-nitrophenyl)amino]-1-bromopropane

HRID 1578304Notes

Reaction equation

HRID 1578304 reaction equation
[C:1]1([N-:7][C:8]2[CH:13]=[CH:12][C:11]([N+:14]([O-:16])=[O:15])=[CH:10][CH:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Br:17][CH2:18][CH2:19][C:20](Cl)=O.B.C1(N(CCCBr)C2C=CC=CC=2)C=CC=CC=1>O1CCCC1>[C:1]1([N:7]([CH2:20][CH2:19][CH2:18][Br:17])[C:8]2[CH:13]=[CH:12][C:11]([N+:14]([O-:16])=[O:15])=[CH:10][CH:9]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 4

HCID 6331BoraneHCID 84944Propanoyl chloride, 3-bromo-HCID 108273293-[N,N-diphenylamino)-1-bromopropaneHCID 86738022N-phenyl-N-(4-nitrophenyl)amide

Product 1

HCID 204826193-[N-phenyl-N-(4-nitrophenyl)amino]-1-bromopropane

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

3-[N-phenyl-N-(4-nitrophenyl)amino]-1-bromopropane is prepared from N-phenyl-N-(4-nitrophenyl)amide with 3-bromopropionyl chloride, followed by reduction with borane in tetrahydrofuran, by a procedure analogous to the preparation of 3-[N,N-diphenylamino]-1-bromopropane in Example 2.

Sources & evidence

ORD record
ord-fbe1168b47914c31979f254b089ef0ec
Source dataset
uspto-grants-1981_09
Patent number
US04292321

Reaction notes

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