Pyridine → tert-Butyl 2-(4-bromophenyl)propan-2-ylcarbamate
Reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([CH3:13])([CH3:12])C(N)=O)=[CH:4][CH:3]=1.FC(F)(F)C(OI(C1C=CC=CC=1)O[C:21](=[O:26])C(F)(F)F)=O.[N:35]1C=CC=CC=1.[C:41]([OH:45])([CH3:44])([CH3:43])[CH3:42]>>[C:41]([O:45][C:21](=[O:26])[NH:35][C:8]([C:5]1[CH:4]=[CH:3][C:2]([Br:1])=[CH:7][CH:6]=1)([CH3:12])[CH3:13])([CH3:44])([CH3:43])[CH3:42]Participants
Procedure
To a suspension of 2-(4-bromophenyl)-2-methylpropanamide (3 g) in tert-butanol (31 mL) was added [bis(trifluoroacetoxy)iodo]benzene (8 g) portionwise at room temperature. The reaction mixture was stirred at reflux temperature for 30 min Pyridine (3 mL) was added to the mixture. After being stirred at reflux temperature for 1 h, the reaction mixture was concentrated to dryness. The residue was dissolved in benzene and washed with 1 M citric acid aqueous solution (2 times), sodium bicarbonate aqueous solution (5 times) then brine. The organics were dried over anhydrous sodium sulfate and concentrated under reduced pressure. Purification by column chromatography (0-20% ethyl acetate in hexanes) gave the product (3.29 g, 84%). 1HNMR (CDCl3) 400 MHz δ: 7.43 (d, J=8.6 Hz, 2H), 7.27 (d, J=8.6 Hz, 2H), 1.59 (br s, 6H), 1.48-1.05 (m, 9H).
Workup
- additionwas added to the mixture
- stirringAfter being stirred
- temperatureat reflux temperature for 1 h
- concentrationthe reaction mixture was concentrated to dryness
- dissolutionThe residue was dissolved in benzene
- washwashed with 1 M citric acid aqueous solution (2 times), sodium bicarbonate aqueous solution (5 times)
- dry with materialThe organics were dried over anhydrous sodium sulfate
- concentrationconcentrated under reduced pressure
- customPurification by column chromatography (0-20% ethyl acetate in hexanes)
Sources & evidence
- ORD record
- ord-68d8ecb862964219a2a954cdcba49525
- Source dataset
- uspto-grants-2013_10
- Patent number
- US08569331B2
Reaction notes
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