Acetic Acid → HCID 12025898, compound

HRID 2298626

Reaction equation

HRID 2298626 reaction equation
[C:1]([C:5]1[O:9][C:8]([CH3:10])=[C:7](C(Cl)=O)[CH:6]=1)([CH3:4])([CH3:3])[CH3:2].C[Si](C=[N+]=[N-])(C)C.[BrH:21].[C:22]([OH:25])(=O)[CH3:23]>C(#N)C>[C:1]([C:5]1[O:9][C:8]([CH3:10])=[C:7]([C:22](=[O:25])[CH2:23][Br:21])[CH:6]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 260Hydrogen BromideHCID 167693TrimethylsilyldiazomethaneHCID 27984945-(Tert-Butyl)-2-Methylfuran-3-Carbonyl Chloride

Product 1

HCID 12025898HCID 12025898, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 1 g (5 mmol) of 5-(tert-butyl)-2-methylfuran-3-carbonyl chloride (Maybridge, Cornwall, UK) dissolved in dry acetonitrile (4 mL) and 6.25 mL (12.5 mmol) of 2 M trimethylsilyldiazomethane in hexanes (Aldrich, Milwaukee, Wis.) was stirred 1.75 h at room temperature and the mixture was cooled on an ice bath for 5 min. To this, 30% hydrogen bromide in acetic acid (2 mL, 10 mmol) was added dropwise over 10 min. This was stirred an additional 20 minutes on an ice bath. Evaporation of the solvents gave 1-[5-(tert-butyl)-2-methyl(3-furyl)]-2-bromoethan-1-one (1 g, 77%) as a brown oil. 1H-NMR (DMSO-d6; 300 MHz) δ6.50 (s, 1H), 4.57(s, 2H), 2.52 (s, 1H), 1.24 (s, 9H). Mass spectrum (LCA, m/z): Calcd. for C11H15O2Br, 259.1 and 261.1 (M+H), found 259.1 and 261.1.

Workup

  1. temperaturethe mixture was cooled on an ice bath for 5 min
  2. customEvaporation of the solvents

Sources & evidence

ORD record
ord-175a621a15c04ba6b0cead3d192e5b80
Source dataset
uspto-grants-2002_12
Patent number
US06492403B1

Linked notes

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