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

HRID 229171Notes

Reaction equation

HRID 229171 reaction equation
C[O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9](=[C:20]2[CH2:25][C:24]([CH3:27])([CH3:26])[CH2:23][C:22]([CH3:29])([CH3:28])[CH2:21]2)[C:10]2[CH:15]=[CH:14][C:13]([NH:16][C:17](=[O:19])[CH3:18])=[CH:12][CH:11]=2)=[CH:5][CH:4]=1.B(Br)(Br)Br>C(Cl)Cl>[OH:2][C:3]1[CH:4]=[CH:5][C:6]([C:9](=[C:20]2[CH2:21][C:22]([CH3:29])([CH3:28])[CH2:23][C:24]([CH3:27])([CH3:26])[CH2:25]2)[C:10]2[CH:15]=[CH:14][C:13]([NH:16][C:17](=[O:19])[CH3:18])=[CH:12][CH:11]=2)=[CH:7][CH:8]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 68654481N-{4-[[4-(methyloxy)phenyl](3,3,5,5-tetramethylcyclohexylidene)methyl]phenyl}acetamide

Product 1

HCID 11199773N-{4-[(4-hydroxyphenyl)(3,3,5,5-tetramethylcyclohexylidene)methyl]phenyl}acetamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
-10 °C

Procedure

N-{4-[[4-(methyloxy)phenyl](3,3,5,5-tetramethylcyclohexylidene)methyl]phenyl}acetamide (57) (0.27 g, 0.69 mmol) was dissolved in CH2Cl2 (25 mL). The mixture was cooled to −10° C. in an ice-acetone bath. To this solution was added 1 M BBr3 in CH2Cl2 (2.1 mL, 2.07 mmol). The reaction mixture was stirred at −10° C. to 0° C. for 3 h, then poured onto ice, extracted with EtOAc (2×60 mL). The combined organic extract was washed with water, brine and dried over Na2SO4. Upon concentration and trituration with 1:1 hexanes:CH2Cl2, compound 58 was obtained as a light brown solid (0.10 g, 39%). mp 118-121° C. 1H NMR (400 MHz, DMSO-d6): δ 0.85 (s, 6H), 0.86 (s, 6H), 1.23 (s, 2H), 1.87 (s, 2H), 1.89 (s, 2H), 1.98 (s, 3H), 6.64 (d, J=8.3 Hz, 2H), 6.89 (d, J=8.5 Hz, 2H), 7.00 (d, J=8.5 Hz, 2H), 7.44 (d, J=8.4 Hz, 2H), 9.24 (s, 1H), 9.84 (s, 1H); LCMS (ES): m/z 378 (M+H)+, 376 (M−H)−. Anal. Calcd for C25H31NO2.1/3H2O: C, 78.29; H, 8.32, N, 3.65; Found: C, 78.33; H, 8.26, N, 3.62.

Workup

  1. additionpoured onto ice
  2. extractionextracted with EtOAc (2×60 mL)
  3. extractionThe combined organic extract
  4. washwas washed with water, brine
  5. dry with materialdried over Na2SO4
  6. concentrationUpon concentration and trituration with 1:1 hexanes

Sources & evidence

ORD record
ord-da6f5b744e0242d093e67c637b481325
Source dataset
uspto-grants-2009_07
Patent number
US07560589B2

Reaction notes

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