Hydrogen Bromide → 2-Hydroxydibenzofuran-3-carboxylic acid

HRID 1081528Notes

Reaction equation

HRID 1081528 reaction equation
C[O:2][C:3]1[C:15]([C:16]([OH:18])=[O:17])=[CH:14][C:6]2[O:7][C:8]3[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=3[C:5]=2[CH:4]=1.Br.BrC>C(O)(=O)C>[OH:2][C:3]1[C:15]([C:16]([OH:18])=[O:17])=[CH:14][C:6]2[O:7][C:8]3[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=3[C:5]=2[CH:4]=1

Participants

5

Reactant 3

HCID 260Hydrogen BromideHCID 6323Methyl BromideHCID 458266HCID 458266, compound

Product 1

HCID 670422-Hydroxydibenzofuran-3-carboxylic acidYield 98%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
30 °C

Procedure

A mixture of 2-methoxydibenzofuran-3-carboxylic acid 21.62 g, (prepared by the method disclosed in Cl. Routier, Ng. Ph. Buu-Hoi, and R. Royer, J. Chem. Soc., 4276 [1956] which is incorporated herein by reference), 48% hydrobromic acid (250 ml) and acetic acid (175 ml) was boiled under reflux, allowing bromomethane to escape, for 2 hrs, removed from the heat source, diluted with 400 ml of water with stirring, and cooled in ice to 30° C. The crystalline product was filtered, washed with water, and dried, to give 19.9 g (98%) of 2-hydroxy-dibenzofuran-3-carboxylic acid, m.p. 301°-2° dec. An analytical sample was prepared by twice recrystallizing a portion from 2-ethoxyethanol, m.p. 301°-303° dec.

Workup

  1. custom(prepared by the method
  2. temperatureunder reflux
  3. customremoved from the heat source
  4. additiondiluted with 400 ml of water
  5. filtrationThe crystalline product was filtered
  6. washwashed with water
  7. customdried

Sources & evidence

ORD record
ord-a3f7a30f625e473983f068af339d9b4b
Source dataset
uspto-grants-1996_12
Patent number
US05587112

Reaction notes

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