Dichloromethane → 2-Benzyloxy-5-nitro-biphenyl

HRID 1157157Notes

Reaction equation

HRID 1157157 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([N+:15]([O-:17])=[O:16])=[CH:11][C:10]=1Br)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(Cl)Cl.[C:22]1(B(O)O)[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>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].O1CCOCC1>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([N+:15]([O-:17])=[O:16])=[CH:11][C:10]=1[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 6344DichloromethaneHCID 62657Potassium Phosphate, TribasicHCID 66827Phenylboronic AcidHCID 220178401-(Benzyloxy)-2-bromo-4-nitrobenzene

Product 1

HCID 589852532-Benzyloxy-5-nitro-biphenylYield 80.4%

Reagents, catalysts & solvents 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 312751,4-DioxaneSolvent

Procedure

To a mixture of 1-benzyloxy-2-bromo-4-nitrobenzene (100 mg, 0.33 mmol), Pd(dppf)Cl2.DCM (12 mg, 0.016 mmol), phenylboronic acid (48 mg, 0.39 mmol) and potassium phosphate (207 mg, 0.98 mmol) was added dioxane under an argon atmosphere. The mixture was stirred overnight at 80 C and filtered. The filtrate was concentrated and purified by flash chromatography (5:1 hexanes/ethyl acetate) to give 2-benzyloxy-5-nitro-biphenyl (81 mg).

Workup

  1. filtrationfiltered
  2. concentrationThe filtrate was concentrated
  3. custompurified by flash chromatography (5:1 hexanes/ethyl acetate)

Sources & evidence

ORD record
ord-cdee2d290ecd4c47865bfeb1d04aef3f
Source dataset
uspto-grants-2010_10
Patent number
US07807672B2

Reaction notes

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