Hydrogen Bromide → HCID 23455899, compound

HRID 262252Notes

Reaction equation

HRID 262252 reaction equation
C(OC([C:6]1[O:7][C:8]2[CH:15]=[CH:14][C:13]([C:16]3[CH:21]=[CH:20][C:19]([CH2:22][C:23]([O:25]CC)=[O:24])=[CH:18][CH:17]=3)=[CH:12][C:9]=2[C:10]=1[CH3:11])=O)C.Br>C(O)(=O)C>[CH3:11][C:10]1[C:9]2[CH:12]=[C:13]([C:16]3[CH:21]=[CH:20][C:19]([CH2:22][C:23]([OH:25])=[O:24])=[CH:18][CH:17]=3)[CH:14]=[CH:15][C:8]=2[O:7][CH:6]=1

Participants

4

Reactant 2

HCID 260Hydrogen BromideHCID 12902869HCID 12902869, compound

Product 1

HCID 23455899HCID 23455899, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of 17 g. of the product of step A in 100 ml. of acetic acid with 35 ml. of 48 percent hydrobromic acid is heated at reflux for three hours, then poured into ice water. This mixture is extracted into dichloromethane, and the extracts are dried to provide 4-(3-methylbenzofuran-5-yl)phenylacetic acid. This intermediate is esterified by heating with a trace of sulfuric acid in ethanol. The product is purified by chromatography on silica gel, eluting with 20 percent dichloromethane in carbon tetrachloride to provide ethyl 4-(3-methylbenzofuran-5-yl)phenylacetate.

Workup

  1. temperatureat reflux for three hours
  2. extractionThis mixture is extracted into dichloromethane
  3. customthe extracts are dried

Sources & evidence

ORD record
ord-d11379427a3746f897e82190441bf3b7
Source dataset
uspto-grants-1979_05
Patent number
US04153721

Reaction notes

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