Water → HCID 18454615, compound

HRID 1271641Notes

Reaction equation

HRID 1271641 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12](Br)=[CH:11][C:10]=1[C:16]([CH3:19])([CH3:18])[CH3:17])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O.CCOC(C)=O.[CH3:27][N:28](C=O)C>[C-]#N.[Zn+2].[C-]#N.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:27]#[N:28])=[CH:11][C:10]=1[C:16]([CH3:19])([CH3:18])[CH3:17])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 962WaterHCID 6228DimethylformamideHCID 8857Ethyl AcetateHCID 184546144-Bromo-2-(1,1-dimethylethyl)-1-(phenylmethoxy)benzene

Product 1

HCID 18454615HCID 18454615, compound

Reagents, catalysts & solvents 2

HCID 11186Zinc cyanide (Zn(CN)2)CatalystHCID 178418397HCID 178418397, compoundCatalyst

Conditions

Temperature
175 °C

Procedure

1-Benzyloxy-4-bromo-2-tert-butyl-benzene made in example 47B (319 mg, 1 mmol), zinc cyanide (129 mg, 1.1 mmol) and Pd(PPh3)4 (34.5 mg, 0.03 mmol) were mixed in 4 mL of DMF then the mixture was heated to 175 ° C. in a microwave reactor (Emrys Optimizer by Personal Chemistry) for 5 minutes. The mixture was cooled to room temperature, and then water and EtOAc were added. The EtOAc extracts were dried over Na2SO4, concentrated and the resulting residue was purified by flash chromatography (5–10% EtOAc/Hexanes) to give the desired nitrile (64 mg). MS (DCI) m/z 238 (M+H)+.

Workup

  1. temperatureThe mixture was cooled to room temperature
  2. dry with materialThe EtOAc extracts were dried over Na2SO4
  3. concentrationconcentrated
  4. customthe resulting residue was purified by flash chromatography (5–10% EtOAc/Hexanes)

Sources & evidence

ORD record
ord-714d2e37992c4086b7d06e9833b705f4
Source dataset
uspto-grants-2007_04
Patent number
US07205409B2

Reaction notes

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