4-Fluorobenzoic Acid → 3-(Chlorosulfonyl)-4-fluorobenzoic acid

HRID 1825807Notes

Reaction equation

HRID 1825807 reaction equation
[Cl:1][S:2]([OH:5])(=O)=[O:3].[F:6][C:7]1[CH:15]=[CH:14][C:10]([C:11]([OH:13])=[O:12])=[CH:9][CH:8]=1>>[Cl:1][S:2]([C:8]1[CH:9]=[C:10]([CH:14]=[CH:15][C:7]=1[F:6])[C:11]([OH:13])=[O:12])(=[O:5])=[O:3]

Participants

3

Reactant 2

HCID 99734-Fluorobenzoic AcidHCID 24638Chlorosulfonic acid

Product 1

HCID 39298913-(Chlorosulfonyl)-4-fluorobenzoic acid

Conditions

Temperature
150 °C

Procedure

Chlorosulphonic acid (100 ml, 1.5 mol) was gradually added to 4-fluorobenzoic acid (43 g, 0.307 mol) with stirring. The clear dark yellow mixture was heated to 150° C. for 24 hours. The yellow solution was cooled back to room temperature and poured onto ice with vigorous stirring. The white precipitate was filtered and pressed dry. The solid was dried overnight in a desiccator under vacuum and over activated silica (54.65 g, 75%). Mp: 116–117° C.; m/z (LC-MS, ESP), RT=4.03 min, (M−−1)=237–239 (ratio 1:3).

Workup

  1. temperatureThe yellow solution was cooled back to room temperature
  2. additionpoured onto ice with vigorous stirring
  3. filtrationThe white precipitate was filtered
  4. custompressed dry
  5. customThe solid was dried overnight in a desiccator under vacuum and over activated silica (54.65 g, 75%)

Sources & evidence

ORD record
ord-51f57334051a4f548cfc21bba1741d8f
Source dataset
uspto-grants-2006_05
Patent number
US07049313B2

Reaction notes

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