Hydrogen Bromide → 5-(2-Bromoacetyl)-2-methoxyphenyl acetate

HRID 2298611Notes

Reaction equation

HRID 2298611 reaction equation
[C:1]([O:4][C:5]1[C:10]([O:11][CH3:12])=[CH:9][CH:8]=[C:7]([C:13](Cl)=[O:14])[CH:6]=1)(=[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:6]=[C:7]([C:13](=[O:14])[CH2:16][Br:23])[CH:8]=[CH:9][C:10]=1[O:11][CH3:12])(=[O:3])[CH3:2]

Participants

7

Reactant 3

HCID 260Hydrogen BromideHCID 167693TrimethylsilyldiazomethaneHCID 185369263-(Chlorocarbonyl)-6-methoxyphenyl acetate

Product 1

HCID 132762285-(2-Bromoacetyl)-2-methoxyphenyl acetate

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 6344DichloromethaneSolventHCID 8058HexaneSolvent

Procedure

Using the procedure in Example 85, step (b), the entire sample of 3-(chlorocarbonyl)-6-methoxyphenyl acetate (as prepared in the previous step) in 5 mL of anhyd CH2Cl2 was treated with 2.09 mL (4.18 mmol) of a 2 M solution of trimethylsilyldiazomethane in hexane and 456 μL (2.28 mmol) of 30 wt % HBr in acetic acid. Chromatography as in Example 85, step (b) followed by recrystallization from CH2Cl2-hexane afforded the title compound as a faintly yellow solid (366 mg, 67%). 1H-NMR (300 MHz, CDCl3) δ7.79 (dd, 1H, J=8.6, 2.2 Hz), 7.70 (d, 1H, 2.2 Hz), 7.03 (d, 1H, 8.6 Hz), 4.38 (s, 2H), 3.92 (s, 3H), and 2.34 (s, 3H).

Workup

  1. customChromatography as in Example 85, step (b) followed by recrystallization from CH2Cl2-hexane

Sources & evidence

ORD record
ord-983af20c4ad84fe98486bfaf7775b1b3
Source dataset
uspto-grants-2002_12
Patent number
US06492403B1

Reaction notes

Loading…