1,4-Dibromobenzene → benzyl N-[3-(4-bromophenyl)propyl]carbamate

HRID 48372Notes

Reaction equation

HRID 48372 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([Br:8])=[CH:4][CH:3]=1.[C:9]1([CH2:15][O:16][C:17]([NH:19][CH2:20][CH:21]=[CH2:22])=[O:18])[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.B1C2CCCC1CCC2.[OH-].[Na+]>Cl[Pd]Cl.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].OO>[Br:8][C:5]1[CH:6]=[CH:7][C:2]([CH2:22][CH2:21][CH2:20][NH:19][C:17]([O:16][CH2:15][C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=2)=[O:18])=[CH:3][CH:4]=1

Participants

8

Reactant 4

HCID 78041,4-DibromobenzeneHCID 14798Sodium HydroxideHCID 789669-Borabicyclo(3.3.1)nonaneHCID 562279Benzyl allylcarbamate

Product 1

HCID 22743235benzyl N-[3-(4-bromophenyl)propyl]carbamateYield 54.1%

Reagents, catalysts & solvents 3

HCID 24290Palladium ChlorideCatalystHCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 784Hydrogen PeroxideSolvent

Procedure

Scheme IVc, step A: 1,4-Dibromobenzene (2 g, 8.5 mmol), (phenylmethoxy)-N-prop-2-enylcarboxamide (1.95 g, 10.1 mmol, prepared in example 8), 9-BBN-dimer (2.7 g, 11 mmol), [1,1′bis(diphenylphosphino)-ferrocene] dichloropalladium (II), PdCl2(dppf), (0.35 g, 0.42 mmol), 3N sodium hydroxide (3 mL), and pH=7 buffer hydrogen peroxide (2:1, 10 mL) were combined in a manner analogous to the procedure described in example 6 to provide the intermediate title compound, N-[3-(4-bromophenyl)propyl](phenylmethoxy)carboxamide, (1.6 g, 54%). Electron spray M.S. 348 (M*+2).

Sources & evidence

ORD record
ord-2b86c3292a894938a3171479a8f43f42
Source dataset
uspto-grants-2004_03
Patent number
US06703425B2

Reaction notes

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