1,2-Dimethoxyethane → Ethyl 5-chloro-2-phenylbenzoate

HRID 1930478Notes

Reaction equation

HRID 1930478 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5](I)=[C:6]([CH:12]=1)[C:7]([O:9][CH2:10][CH3:11])=[O:8].C(COC)OC.[C:20]1(B(O)O)[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.C([O-])([O-])=O.[K+].[K+]>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.O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[C:6]([CH:12]=1)[C:7]([O:9][CH2:10][CH3:11])=[O:8]

Participants

7

Reactant 4

HCID 80711,2-DimethoxyethaneHCID 11430Potassium CarbonateHCID 66827Phenylboronic AcidHCID 51341862Ethyl 5-chloro-2-iodobenzoate

Product 1

HCID 59830347Ethyl 5-chloro-2-phenylbenzoateYield 91%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolvent

Procedure

A degassed mixture of ethyl 5-chloro-2-iodobenzoate (0.621 g, 2.00 mmol), Pd(PPh3)4 (0.116 mg, 0.1 mmol), dimethoxyethane (20 mL), phenylboronic acid (0.268 g, 2.2 mmol), K2CO3 (0.829 g, 6.0 mmol), and water (5 mL) was heated under reflux for 6 h. Solvent was removed under reduced pressure. The residue was diluted with sat. NH4Cl (15 mL) and extracted with EtOAc (2×30 mL). The combined organic layers were dried (MgSO4) and concentrated. The crude product was purified by chromatography to afford ethyl 5-chloro-2-phenylbenzoate (0.473 g, 91%) as colorless oil. MS (ESI) m/z: 261.0 (M+H+).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 6 h
  3. customSolvent was removed under reduced pressure
  4. additionThe residue was diluted with sat. NH4Cl (15 mL)
  5. extractionextracted with EtOAc (2×30 mL)
  6. dry with materialThe combined organic layers were dried (MgSO4)
  7. concentrationconcentrated
  8. customThe crude product was purified by chromatography

Sources & evidence

ORD record
ord-b3adbc6696bb44d09053dd8547dc860d
Source dataset
uspto-grants-2012_05
Patent number
US08188113B2

Reaction notes

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