Hydrogen Bromide → HCID 13652182, compound

HRID 2298608Notes

Reaction equation

HRID 2298608 reaction equation
[C:1]([O:4][C:5]1[CH:10]=[CH:9][C:8]([C:11](Cl)=[O:12])=[CH:7][C:6]=1[O:14][CH3:15])(=[O:3])[CH3:2].[CH3:16][Si](C=[N+]=[N-])(C)C.[BrH:23]>C(Cl)Cl.CCCCCC.C(O)(=O)C>[C:1]([O:4][C:5]1[CH:10]=[CH:9][C:8]([C:11](=[O:12])[CH2:16][Br:23])=[CH:7][C:6]=1[O:14][CH3:15])(=[O:3])[CH3:2]

Participants

7

Reactant 3

HCID 260Hydrogen BromideHCID 924974-Acetoxy-3-methoxybenzoyl chlorideHCID 167693Trimethylsilyldiazomethane

Product 1

HCID 13652182HCID 13652182, compoundYield 97%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 6344DichloromethaneSolventHCID 8058HexaneSolvent

Procedure

To a solution of 1.09 g (4.6 mmol) of 4-(chlorocarbonyl)-2-methoxyphenyl acetate (as prepared in the precious step) in 10 mL of anhyd CH2Cl2 was added 10.0 mL (20.0 mmol) of a 2 M solution of trimethylsilyldiazomethane in hexane. After stirring 2 h at room temperature, the mixture was cooled (0° C.) and 3.20 mL (16.0 mmol) of 30 wt % HBr in acetic acid was added dropwise (gas evolution). After stirring 5 min, the mixture was concentrated in vacuo and rapidly chromatographed on a 10 g silica SPE column (Waters Sep-Pak) with CH2Cl2 to afford the title compound as a light yellow crystalline solid (1.28 g, 97%). 1H-NMR (300 MHz, CDCl3) δ7.63 (d, 1H, 1.9 Hz), 7.59 (dd, 1H, J=8.2, 1.9 Hz), 7.16 (d, 1H, 8.2 Hz), 4.43 (s, 2H), 3.91 (s, 3H), and 2.35 (s, 3H).

Workup

  1. additionwas added dropwise (gas evolution)
  2. stirringAfter stirring 5 min
  3. concentrationthe mixture was concentrated in vacuo
  4. customrapidly chromatographed on a 10 g silica SPE column (Waters Sep-Pak) with CH2Cl2

Sources & evidence

ORD record
ord-944cd02adacb49acba3885d561a0cd4f
Source dataset
uspto-grants-2002_12
Patent number
US06492403B1

Reaction notes

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