Pyridine → 2,6-Dibromo-4-fluorobenzyl acetate

HRID 519281Notes

Reaction equation

HRID 519281 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[C:4]([Br:9])[C:3]=1[CH2:10][OH:11].N1C=CC=CC=1.[C:18](Cl)(=[O:20])[CH3:19]>C(Cl)Cl>[C:18]([O:11][CH2:10][C:3]1[C:2]([Br:1])=[CH:7][C:6]([F:8])=[CH:5][C:4]=1[Br:9])(=[O:20])[CH3:19]

Participants

5

Reactant 3

HCID 1049PyridineHCID 6367Acetyl chlorideHCID 58043943(2,6-Dibromo-4-fluorophenyl)methanol

Product 1

HCID 670165932,6-Dibromo-4-fluorobenzyl acetateYield 87%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (2,6-dibromo-4-fluorophenyl)methanol (104l) (20 g, 71 mmol) in CH2Cl2 (500 mL) at 0° C. was added pyridine (8.4 g, 107 mmol) and acetyl chloride (8.3 g, 107 mmol). The mixture was stirred at room temperature for 5 h. TLC showed the start material disappeared. The reaction was evaporated in vacuum and the residue was purified by silica-gel column chromatography eluting with petroleum ether/ethyl acetate (from 50:1 to 20:1) to give 104m as a white solid (20g, 87%). MS: [M-Oac]+ 267. 1H NMR (500 MHz, CDCl3) δ 7.36 (d, J=7.5, 2H), 5.38 (s, 2H), 2.10 (s, 3H)

Workup

  1. customThe reaction was evaporated in vacuum
  2. customthe residue was purified by silica-gel column chromatography
  3. washeluting with petroleum ether/ethyl acetate (from 50:1 to 20:1)

Sources & evidence

ORD record
ord-ffc4a879204b4765ba6bc3529aa5ae70
Source dataset
uspto-grants-2015_08
Patent number
US09115152B2

Reaction notes

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