Benzyl Alcohol → Benzyl 4-fluorobenzoate

HRID 2190552Notes

Reaction equation

HRID 2190552 reaction equation
[F:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][CH:3]=1.[Cl-].[CH2:12](O)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C(N(C(C)C)CC)(C)C>CCOCC.CN(C1C=CN=CC=1)C.C(Cl)Cl.CN(C=O)C>[CH2:12]([O:7][C:6](=[O:8])[C:5]1[CH:9]=[CH:10][C:2]([F:1])=[CH:3][CH:4]=1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

9

Reactant 4

HCID 244Benzyl AlcoholHCID 312ChlorideHCID 99734-Fluorobenzoic AcidHCID 81531Diisopropylethylamine

Product 1

HCID 579322Benzyl 4-fluorobenzoateYield 60.4%

Reagents, catalysts & solvents 4

HCID 142844-(Dimethylamino)pyridineCatalystHCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

A mixture of 4-fluorobenzoic acid (1.0 g, 7.13 mmol) in Et2O was treated with oxallyl chloride (760 mL, 8.55 mmol) and a catalytic amount of DMF. The mixture was then stirred until the evolution of gas stopped. The mixture was then filtered and concentrated under reduced pressure. The residue was dissolved in a small volume of CH2Cl2 and the solution was added in a drop wise manner to a mixture of benzyl alcohol (770 mg, 7.13 mmol), diisopropyl ethyl amine (2.49 mL, 14.3 mmol) and a catalytic amount of DMAP in CH2Cl2 (20 mL). After stirring overnight the reaction mixture was concentrated and the residue was passed through a silica gel plug with 10% Et2O in hexanes to afford the product (991 mg, Yield: 60%). FIRMS m/z calcd for C14H11O2F [M+H]+: 230.0743. Found: 230.0742.

Workup

  1. filtrationThe mixture was then filtered
  2. concentrationconcentrated under reduced pressure
  3. dissolutionThe residue was dissolved in a small volume of CH2Cl2
  4. stirringAfter stirring overnight the reaction mixture
  5. concentrationwas concentrated

Sources & evidence

ORD record
ord-f1f840b31fb94365a5e74530f11f40ad
Source dataset
uspto-grants-2012_12
Patent number
US08324385B2

Reaction notes

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