Bromine → Methyl 2,3-methylenedioxy-4-methoxy-5-bromobenzoate

HRID 976255Notes

Reaction equation

HRID 976255 reaction equation
[CH2:1]1[O:13][C:12]2[C:3](=[C:4]([CH:9]=[CH:10][C:11]=2[O:14][CH3:15])[C:5]([O:7][CH3:8])=[O:6])[O:2]1.[Br:16]Br>C(Cl)(Cl)Cl>[CH2:1]1[O:13][C:12]2[C:3](=[C:4]([CH:9]=[C:10]([Br:16])[C:11]=2[O:14][CH3:15])[C:5]([O:7][CH3:8])=[O:6])[O:2]1

Participants

4

Reactant 2

HCID 24408BromineHCID 19967040HCID 19967040, compound

Product 1

HCID 13170923Methyl 2,3-methylenedioxy-4-methoxy-5-bromobenzoateYield 93.2%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Compound 122 (5.56 g, 25.6 mmol) was dissolved in anhydrous chloroform. Bromine (4.5 g, 28.5 mmol) was added dropwise over 2 hours at 5°-8° C. Then the mixture was maintained for an additional 2 hours at the same temperature. After the usual workup, 6.9 g of white solid 123 was obtained (88% yield). m.p. 165°-6° C. (crystallized from ethyl acetate). IR cm-1 1710 (s, C=O), 1425, 1400 (s, C--O); MS m/z (%): 288 (M+, 100), 290 (M+2, 96); 1H NMR δ ppm 3.91 (s, 3H, OCH3), 4.14 (s, 3H, ArOCH3), 6.10 (s, 2H, OCH2O), 7.65 (s, 1H, 6-ArH); Anal. (C10H9O5Br) C, H, Br.

Workup

  1. temperatureThen the mixture was maintained for an additional 2 hours at the same temperature

Sources & evidence

ORD record
ord-ed5d5bab11e248d3b87016569709c47d
Source dataset
uspto-grants-1997_03
Patent number
US05612341

Reaction notes

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