Carbon tetrabromide → 5-(Benzyloxy)-6-but-3-enylquinoline

HRID 47957Notes

Reaction equation

HRID 47957 reaction equation
[CH2:1]([O:8][C:9]1[C:18]([CH2:19]O)=[CH:17][CH:16]=[C:15]2[C:10]=1[CH:11]=[CH:12][CH:13]=[N:14]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(Br)(Br)(Br)Br.[C:26]1(P(C2C=CC=CC=2)C2C=CC=CC=2)[CH:31]=CC=C[CH:27]=1.C([Mg]Br)C=C>ClCCl.O1CCCC1>[CH2:1]([O:8][C:9]1[C:18]([CH2:19][CH2:31][CH:26]=[CH2:27])=[CH:17][CH:16]=[C:15]2[C:10]=1[CH:11]=[CH:12][CH:13]=[N:14]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 23431816[5-(Benzyloxy)quinolin-6-yl]methanolHCID 178455850HCID 178455850, compound

Product 1

HCID 234318275-(Benzyloxy)-6-but-3-enylquinoline

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

Treatment of [5-(benzyloxy)quinolin-6-yl]methanol with carbontetrabromide and triphenylphosphine in dichloromethane and subsequent treatment with allyl magnesiumbromide in tetrahydrofu ran following the procedure described for Example 1, step 1 provides 5-(benzyloxy)-6-but-3-enylquinoline.

Sources & evidence

ORD record
ord-3601a4ff3252475bba70f33fa073f404
Source dataset
uspto-grants-2004_03
Patent number
US06700001B2

Reaction notes

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