Benzonitrile, 4-bromo- → HCID 86709844, compound

HRID 920868Notes

Reaction equation

C([O-])(=O)C(C)(C)C.[C:8]([O:12][C:13]([O:15][C:16]1[CH:21]=[CH:20][CH:19]=[C:18]([C:22]([O:24][CH2:25][CH3:26])=[O:23])[C:17]=1[Zn+])=[O:14])([CH3:11])([CH3:10])[CH3:9].Br[C:29]1[CH:36]=[CH:35][C:32]([C:33]#[N:34])=[CH:31][CH:30]=1.COC1C=CC=C(OC)C=1C1C=CC=CC=1P(C1CCCCC1)C1CCCCC1.[NH4+].[Cl-]>C1COCC1.CC([O-])=O.CC([O-])=O.[Pd+2]>[CH2:25]([O:24][C:22]([C:18]1[C:17]([C:29]2[CH:36]=[CH:35][C:32]([C:33]#[N:34])=[CH:31][CH:30]=2)=[C:16]([O:15][C:13]([O:12][C:8]([CH3:11])([CH3:10])[CH3:9])=[O:14])[CH:21]=[CH:20][CH:19]=1)=[O:23])[CH3:26].[C:33](#[N:34])[C:32]1[CH:35]=[CH:36][CH:29]=[CH:30][CH:31]=1

Participants

Conditions

Temperature: 22 °C

Procedure

Furthermore, (2-((Tert-butoxycarbonyl)oxy)-6-(ethoxycarbonyl)phenyl)zinc pivalate (1u) was dissolved in 2.0 mL of dry THF and 4-bromobenzonitrile (164 mg, 0.91 mmol) and Pd(OAc)2 (4 mg, 0.02 mmol) as well as S-Phos (16 mg, 0.04 mmol) were added and the mixture was stirred at 22° C. for 12 h. Then sat. aq. NH4Cl (10 mL) was added and the aqueous layer was extracted with EtOAc (3×20 mL). The combined organic phases were dried (Na2SO4). Evaporation of the solvents in vacuo and purification by flash chromatography (silica gel, ihexane/EtOAc=12:1 to 6:1) afforded the benzonitrile ethyl 4′-cyano-6-((tert-butoxycarbonyl)oxy)-[1,1′-biphenyl]-2-carboxylate (262 mg, 79%) as a pale yellow oil (entry 27).

Workup

extractionthe aqueous layer was extracted with EtOAc (3×20 mL)
dry with materialThe combined organic phases were dried (Na2SO4)
customEvaporation of the solvents
customin vacuo and purification by flash chromatography (silica gel, ihexane/EtOAc=12:1 to 6:1)

Sources & evidence

ORD record: ord-ad9075a46eb448ff8a1aaa37cd851fac
Source dataset: uspto-grants-2016_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09273070B2

Reaction notes

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