Acetic Acid → 4-(3-Fluoro-4-hydroxyphenyl)benzoic acid

HRID 2372256Notes

Reaction equation

HRID 2372256 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:10]2[CH:15]=[CH:14][C:13]([C:16]([OH:18])=[O:17])=[CH:12][CH:11]=2)[CH:5]=[CH:6][C:7]=1[O:8]C.C(O)(=O)C.Br>O>[F:1][C:2]1[CH:3]=[C:4]([C:10]2[CH:15]=[CH:14][C:13]([C:16]([OH:18])=[O:17])=[CH:12][CH:11]=2)[CH:5]=[CH:6][C:7]=1[OH:8]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 260Hydrogen BromideHCID 12031663'-Fluoro-4'-methoxy-[1,1'-biphenyl]-4-carboxylic acid

Product 1

HCID 8361394-(3-Fluoro-4-hydroxyphenyl)benzoic acidYield 92.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To 42 g (0.17 mol) of the above 3'-fluoro-4'-methoxybiphenyl-4-carboxylic acid were added 1.7 l of acetic acid and 300 ml of 48% hydrogen bromide solution, which was refluxed for 20 hours, poured into 3.5 l of water and air cooled. The precipitated crystal was filtered to obtain 36.4 g (yield: 92%) of 3'-fluoro-4'-hydroxybiphenyl-4-carboxylic acid.

Workup

  1. temperaturewas refluxed for 20 hours
  2. temperaturecooled
  3. filtrationThe precipitated crystal was filtered

Sources & evidence

ORD record
ord-6076c2dec0714be3891e41252d92af29
Source dataset
uspto-grants-1992_03
Patent number
US05098602

Reaction notes

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