Benzonitrile, 4-bromo- → Ethyl 4-(4-cyanophenyl)benzoate

HRID 1292327Notes

Reaction equation

HRID 1292327 reaction equation
[I-].[C:2]([C:7]1[CH:12]=[CH:11][C:10]([Zn+])=[CH:9][CH:8]=1)([O:4][CH2:5][CH3:6])=[O:3].Br[C:15]1[CH:22]=[CH:21][C:18]([C:19]#[N:20])=[CH:17][CH:16]=1>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.C1COCC1>[C:19]([C:18]1[CH:21]=[CH:22][C:15]([C:10]2[CH:11]=[CH:12][C:7]([C:2]([O:4][CH2:5][CH3:6])=[O:3])=[CH:8][CH:9]=2)=[CH:16][CH:17]=1)#[N:20]

Participants

5

Reactant 2

HCID 12162Benzonitrile, 4-bromo-HCID 178469116HCID 178469116, compound

Product 1

HCID 12143161Ethyl 4-(4-cyanophenyl)benzoateYield 80.1%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

4-Carbethoxyphenylzinc iodide (2.16 mmol, in about 10 mL THF) was transferred via a cannula to a THF solution of 5 mole-% Pd(PPh3)4 (0.127 g, 0.11 mmol) and 4-bromobenzonitrile (0.400 g, 2.19 mmol) at room temperature under an argon atmosphere. The solution was then stirred for 3 hours. The reaction product was isolated by a procedure similar to that described in Example 3. Ethyl 4-(4-cyanophenyl)benzoate (Entry 4 in Table VIII, 0.433 g, 1.73 mmol) in 80% yield was obtained as a crystalline solid: mp 114°-115° C.; 1H NMR (360 MHz) δ7.60-8.21 (m, 8H), 4.42 (q, J=7.1 Hz, 2H), 1.42 (t, J=7.1 Hz, 3H); 13C NMR δ165.9, 144.2, 143.1, 132.5, 130.4, 130.1, 127.7, 127.0, 118.5, 111.6, 61.0, 14.2; IR (CCl4) ν2981, 2231, 1722, 1608, 1276, 1109 cm-1. HREI calcd. for C16H13NO2 m/e 251.0947, found 251.0949. Anal. calcd. for C16H13NO2 : C, 76.48; H, 5.21; N, 5.57, Found: C, 76.25; H, 5.17; N, 5.31.

Workup

  1. customat room temperature
  2. customThe reaction product was isolated by a procedure similar to

Sources & evidence

ORD record
ord-cb3dac6877d74754ae6682a4da9dc584
Source dataset
uspto-grants-1998_05
Patent number
US05756653

Reaction notes

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