Boron tribromide → N-{4-[(4-Hydroxy-phenyl)-(3,3,5,5-tetramethylcyclohexylidene)-methyl]phenyl}-methanesulfonamide

HRID 229254Notes

Reaction equation

HRID 229254 reaction equation
C[O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9](=[C:21]2[CH2:26][C:25]([CH3:28])([CH3:27])[CH2:24][C:23]([CH3:30])([CH3:29])[CH2:22]2)[C:10]2[CH:15]=[CH:14][C:13]([NH:16][S:17]([CH3:20])(=[O:19])=[O:18])=[CH:12][CH:11]=2)=[CH:5][CH:4]=1.B(Br)(Br)Br>ClCCl>[OH:2][C:3]1[CH:8]=[CH:7][C:6]([C:9](=[C:21]2[CH2:22][C:23]([CH3:30])([CH3:29])[CH2:24][C:25]([CH3:28])([CH3:27])[CH2:26]2)[C:10]2[CH:15]=[CH:14][C:13]([NH:16][S:17]([CH3:20])(=[O:19])=[O:18])=[CH:12][CH:11]=2)=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 68654454N-{4-[(4-Methoxy-phenyl)-(3,3,5,5-tetramethyl-cyclohexylidene)-methyl]phenyl}-methanesulfonamide

Product 1

HCID 57757232N-{4-[(4-Hydroxy-phenyl)-(3,3,5,5-tetramethylcyclohexylidene)-methyl]phenyl}-methanesulfonamideYield 72%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-2.5 °C

Procedure

To a solution of N-{4-[(4-methoxy-phenyl)-(3,3,5,5-tetramethyl-cyclohexylidene)methyl]-phenyl}-methanesulfonamide (180) (0.25 g, 0.585 mmol) in dry dichloromethane (20 mL) was slowly added BBr3 (1 N in dichloromethane) (1.75 mL, 1.75 mmol) at −5 to 0° C. The reaction mixture was stirred at −5 to 0° C. under nitrogen for 3 h. The reaction mixture was poured onto ice and stirred for several minutes. The quenched reaction mixture was transferred to a separatory funnel and the layers were separated. The aqueous layer was extracted with EtOAc and the organic extracts were combined, washed with brine, dried over MgSO4, filtered, and concentrated to give an off white solid. The solid was triturated with hexanes followed by dichloromethane. The product was filtered, washed with methanol, and dried to give 0.174 g (72%) of compound 181 as a white powder. 1H NMR (400 MHz, DMSO-d6): δ 0.86 (s, 12H), 1.23 (s, 2H), 1.86 (s, 2H), 1.89 (s, 2H), 2.94 (s, 3H), 6.64 (d, J=8.6 Hz, 2H), 6.90 (d, J=8.5 Hz, 2H), 7.06 (s, 2H), 7.07 (s, 2H), 9.25 (s, 1H), 9.64 (s, 1H). HRMS (ESI) calcd for C24H30NO3S: 412.1946 (M−H)−. Found: 412.1942.

Workup

  1. customat −5 to 0° C
  2. additionThe reaction mixture was poured onto ice
  3. stirringstirred for several minutes
  4. customThe quenched reaction mixture
  5. customwas transferred to a separatory funnel
  6. customthe layers were separated
  7. extractionThe aqueous layer was extracted with EtOAc
  8. washwashed with brine
  9. dry with materialdried over MgSO4
  10. filtrationfiltered
  11. concentrationconcentrated
  12. customto give an off white solid
  13. customThe solid was triturated with hexanes
  14. filtrationThe product was filtered
  15. washwashed with methanol
  16. customdried

Sources & evidence

ORD record
ord-7dc49f46b93c4e8dac182edb791f7ed9
Source dataset
uspto-grants-2009_07
Patent number
US07560589B2

Reaction notes

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