Nitrite → 3-Hydroxy-5-(pentafluorosulfanyl)benzoic acid
Reaction equation
N[C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([S:11]([F:16])([F:15])([F:14])([F:13])[F:12])[CH:10]=1)[C:5]([OH:7])=[O:6].N([O-])=[O:18].[Na+].N([O-])=O>S(=O)(=O)(O)O.O>[OH:18][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([S:11]([F:16])([F:15])([F:14])([F:13])[F:12])[CH:10]=1)[C:5]([OH:7])=[O:6]Participants
6
Conditions
- Temperature
- -5 °C
Procedure
3-Amino-5-pentafluorosulfanylbenzoic acid (O6.007; 3.9 g) was dissolved in 35% sulfuric acid (120 ml) and cooled to −5° C., and a solution of sodium nitrite (1.1 g) in water (100 ml) was added dropwise within 10 min. After 40 min, further nitrite solution was added (2 ml), and another 2 ml and 1 ml after a further 20 min in each case. Then the cooling bath was removed and the mixture was heated to 100° C. After 5 h, the mixture was cooled and the solution was decanted. The clear, acidic solution was extracted five times with ethyl acetate. The combined extracts were dried over magnesium sulfate, filtered and concentrated. The crude product was recrystallized from ethyl acetate/heptane. 3.6 g of the desired compound were obtained.
Workup
- waitanother 2 ml and 1 ml after a further 20 min in each case
- customThen the cooling bath was removed
- temperaturethe mixture was heated to 100° C
- waitAfter 5 h
- temperaturethe mixture was cooled
- customthe solution was decanted
- extractionThe clear, acidic solution was extracted five times with ethyl acetate
- dry with materialThe combined extracts were dried over magnesium sulfate
- filtrationfiltered
- concentrationconcentrated
- customThe crude product was recrystallized from ethyl acetate/heptane
Sources & evidence
- ORD record
- ord-d53248dd9b114fd1acf8a96417c0fe0a
- Source dataset
- uspto-grants-2015_07
- Patent number
- US09079906B2
Reaction notes
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