Ethyl Acetate → N-{4-[(6-hydroxy-3-methyl-2-phenyl-1-naphthalenyl)oxy]phenyl}ethanesulfonamide

HRID 1993005Notes

Reaction equation

HRID 1993005 reaction equation
C[O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[C:9]([O:13][C:14]1[CH:19]=[CH:18][C:17]([NH:20][S:21]([CH2:24][CH3:25])(=[O:23])=[O:22])=[CH:16][CH:15]=1)=[C:8]([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[C:7]([CH3:32])=[CH:6]2.B(Br)(Br)Br.CCOC(C)=O>C(Cl)Cl>[OH:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[C:9]([O:13][C:14]1[CH:19]=[CH:18][C:17]([NH:20][S:21]([CH2:24][CH3:25])(=[O:23])=[O:22])=[CH:16][CH:15]=1)=[C:8]([C:26]1[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=1)[C:7]([CH3:32])=[CH:6]2

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 25134Boron tribromideHCID 68539412N-{4-[(6-methoxy-3-methyl-2-phenyl-1-naphthalenyl)oxy]phenyl}ethanesulfonamide

Product 1

HCID 11654958N-{4-[(6-hydroxy-3-methyl-2-phenyl-1-naphthalenyl)oxy]phenyl}ethanesulfonamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirring solution of 271 (0.14 g, 0.31 mmol) in 6 mL CH2Cl2 (6 mL), chilled to −20° C. under N2, was added BBr3 (0.24 g, 0.94 mmol) dropwise, via syringe, over 1 minute. After 90 min at −20° C. the r×n was poured over 50 g ice followed by EtOAc (50 mL). The EtOAC layer was washed with brine (50 mL), dried (Na2SO4) and concentrated to a viscous yellow oil that was purified by column chromatography using a gradient of 100% DCM to 1% MeOH: CH2Cl2 to yield a foam. The foam is crystallized from EtOAc/hexanes to yield the title compound 272, as a light yellow solid (72 mg, 55%). 1H NMR (400 MHz, DMSO-d6): δ 1.13 (t, J=7.3 Hz, 3H), 2.13 (s, 3H), 4.01 (q, J=7.3 Hz, 2H), 6.53 (d, J=8.9 Hz, 2H), 6.94 (d, J=8.9 Hz, 2H), 6.97 (dd, J1=2.3 Hz, J2=9.1 Hz, 1H), 7.11-7.30 (m, 5H), 7.54 (s, 1H), 7.55 (d, J=8.8 Hz, 1H), 9.40 (s, 1H), 9.81 (s, 1H).

Workup

  1. washThe EtOAC layer was washed with brine (50 mL)
  2. dry with materialdried (Na2SO4)
  3. concentrationconcentrated to a viscous yellow oil that
  4. customwas purified by column chromatography
  5. customCH2Cl2 to yield a foam
  6. customThe foam is crystallized from EtOAc/hexanes

Sources & evidence

ORD record
ord-f07d5f1e785f4c52a5099d639ca32962
Source dataset
uspto-grants-2010_01
Patent number
US07649093B2

Reaction notes

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