Acetic Acid Mixture with Hydrobromic Acid → HCID 23132794, compound

HRID 2062109Notes

Reaction equation

HRID 2062109 reaction equation
[F:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([O:12]C)=[C:4]([C:14]([OH:16])=[O:15])[CH:3]=1.Br.CC(O)=O>>[F:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([OH:12])=[C:4]([C:14]([OH:16])=[O:15])[CH:3]=1

Participants

3

Reactant 2

HCID 21893785Acetic Acid Mixture with Hydrobromic AcidHCID 66701185HCID 66701185, compound

Product 1

HCID 23132794HCID 23132794, compoundYield 81.4%

Conditions

Temperature
80 °C

Procedure

To 10.1 g 4-fluoro-1-methoxynaphthalene-2-carboxylic acid 55 mL HBr/HOAc were added and the mixture was stirred and heated. After 30 min at 60° C. another 7.5 mL of HBr/HOAc were added, and after an additional 30 min at 80° C. the mixture was cooled to ambient temperature and left standing overnight. The reaction was then poured into ice/water and the precipitated solid was filtered and washed with water, followed by 1% ether in heptane and then by heptane. The solid was dried in vacuo at 40° C. to yield 7.7 g 4-fluoro-1-hydroxynaphthalene-2-carboxylic acid.

Workup

  1. temperatureheated
  2. waitleft
  3. filtrationthe precipitated solid was filtered
  4. washwashed with water
  5. customThe solid was dried in vacuo at 40° C.

Sources & evidence

ORD record
ord-328d63d776c54464825c2c7e30503545
Source dataset
uspto-grants-2012_10
Patent number
US08283479B2

Reaction notes

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