Dichloromethane → HCID 131722609, compound

HRID 1066364Notes

Reaction equation

HRID 1066364 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7](O)[CH:6]=[CH:5]2.[O-]S(C(F)(F)F)(=O)=O.S(OS(C(F)(F)F)(=O)=O)(C(F)(F)F)(=O)=O.N1C=CC=CC=1.Br[CH2:43][C:44]1[CH:49]=[CH:48][C:47](Cl)=[CH:46][C:45]=1/[CH:51]=[CH:52]/[C:53]([O:55][CH2:56][CH3:57])=[O:54].C(Cl)[Cl:59]>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.[Fe+2].C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd]>[Cl:59][C:48]1[CH:47]=[CH:46][C:45](/[CH:51]=[CH:52]/[C:53]([O:55][CH2:56][CH3:57])=[O:54])=[C:44]([CH2:43][C:7]2[CH:6]=[CH:5][C:4]3[C:9](=[CH:10][CH:11]=[C:2]([F:1])[CH:3]=3)[CH:8]=2)[CH:49]=1

Participants

8

Reactant 5

HCID 6344DichloromethaneHCID 2758875TrifluoromethanesulfonateHCID 16724944HCID 16724944, compoundHCID 21198699HCID 21198699, compoundHCID 211987116-Fluoronaphthalen-2-ol

Product 1

HCID 131722609HCID 131722609, compoundYield 47%

Reagents, catalysts & solvents 2

HCID 635956Ferrocene-1,1'-bis-(diphenylphosphine)CatalystHCID 6505921(1E,4E)-1,5-diphenylpenta-1,4-dien-3-one; palladiumCatalyst

Procedure

The naphthol of Step 3 was converted to the triflate with triflic anhydride/pyridine in CH2Cl2 at 0° C. This was coupled with the organozinc of the benzyl bromide of step 2 in example 13, with dppf and Pd(dba)2. This yielded the title compound in 47% yield after purification by silica gel chromatography (10% EtOAc in hexane).

Sources & evidence

ORD record
ord-0a04904e98314476a7fb1f2be3e554d6
Source dataset
uspto-grants-2001_06
Patent number
US06242493B1

Reaction notes

Loading…