Benzyl chloroformate → Methyl 3-cyano-4-hydroxybenzoate

HRID 222919Notes

Reaction equation

HRID 222919 reaction equation
[OH:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][C:3]=1I.C[CH2:14][N:15](C(C)C)C(C)C.ClC(OCC1C=CC=CC=1)=O>C1COCC1>[C:14]([C:3]1[CH:4]=[C:5]([CH:10]=[CH:11][C:2]=1[OH:1])[C:6]([O:8][CH3:9])=[O:7])#[N:15]

Participants

5

Reactant 3

HCID 10387Benzyl chloroformateHCID 81531DiisopropylethylamineHCID 11346465Methyl 4-hydroxy-3-iodobenzoate

Product 1

HCID 11769089Methyl 3-cyano-4-hydroxybenzoateYield 100%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 2 (0.376 mol), DIEA (196 mL, 1.13 mol) and THF (200 mL) was added benzyl chloroformate (59.0 mL, 0.414 mol) dropwise. After the reaction solution was stirred at room temperature for 1 hr, the solution was concentrated on a rotovap. The residue was partitioned between sat. NaHCO3 (300 mL) and dichloromethane and the aqueous phase extracted with additional dichloromethane (100 mL×3). The combined dichloromethane layers were dried over sodium sulfate, filtered, and concentrated in vacuo to give product 3 (0.376 mol).

Workup

  1. concentrationthe solution was concentrated on a rotovap
  2. customThe residue was partitioned between sat. NaHCO3 (300 mL) and dichloromethane
  3. extractionthe aqueous phase extracted with additional dichloromethane (100 mL×3)
  4. dry with materialThe combined dichloromethane layers were dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-361118b265a74da799e0b90c7a04bd67
Source dataset
uspto-grants-2012_06
Patent number
US08207340B2

Reaction notes

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