Benzyl Bromide → HCID 67144510, compound

HRID 2273703Notes

Reaction equation

HRID 2273703 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:11]([O:13][CH3:14])=[O:12])=[C:6](B(O)O)[CH:7]=1.[CH2:15](Br)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.C([O-])([O-])=O.[K+].[K+]>O1CCCC1.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]>[CH2:15]([C:6]1[CH:7]=[C:2]([F:1])[CH:3]=[CH:4][C:5]=1[C:11]([O:13][CH3:14])=[O:12])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

6

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 4374269[5-Fluoro-2-(methoxycarbonyl)phenyl]boronic acid

Product 1

HCID 67144510HCID 67144510, compound

Reagents, catalysts & solvents 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 8028TetrahydrofuranSolvent

Procedure

5-Fluoro-2-(methoxycarbonyl)phenylboronic acid (1.00 g), benzyl bromide (0.50 mL), K2CO3 (1.75 g), and [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II) (PdCl2(dppf)) (0.17 g) were stirred in tetrahydrofuran (20 mL) at 60° C. for 24 hours. The reaction mixture was chromatographed on silica gel with 2% ethyl acetate/hexanes.

Workup

  1. customThe reaction mixture was chromatographed on silica gel with 2% ethyl acetate/hexanes

Sources & evidence

ORD record
ord-75f72bcb67de4d22b39b09faf9df0113
Source dataset
uspto-grants-2015_09
Patent number
US09125913B2

Reaction notes

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