Boron tribromide → 11-(4-Hydroxy-phenyl)-benzo[b]naphtho[2,3-d]thiophen-3-ol

HRID 1873129Notes

Reaction equation

HRID 1873129 reaction equation
B(Br)(Br)Br.[CH2:5]([C:12]1[S:16][C:15]2[CH:17]=[C:18]([O:21]C)[CH:19]=[CH:20][C:14]=2[C:13]=1[C:23]([C:25]1[CH:30]=[CH:29][C:28]([O:31]C)=[CH:27][CH:26]=1)=O)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1>ClCCl>[OH:31][C:28]1[CH:27]=[CH:26][C:25]([C:23]2[C:13]3[C:14]4[CH:20]=[CH:19][C:18]([OH:21])=[CH:17][C:15]=4[S:16][C:12]=3[CH:5]=[C:6]3[C:7]=2[CH:8]=[CH:9][CH:10]=[CH:11]3)=[CH:30][CH:29]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 15481275(2-Benzyl-6-methoxy-benzo[b]thiophen-3-yl)-(4-methoxy-phenyl)-methanone

Product 1

HCID 1548123611-(4-Hydroxy-phenyl)-benzo[b]naphtho[2,3-d]thiophen-3-olYield 102.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Boron tribromide (5 mL, 52.9 mmol) was added slowly to a stirrred solution of (2-benzyl-6-methoxy-benzo[b]thiophen-3-yl)-(4-methoxy-phenyl)-methanone (2.30 g, 5.92 mmol) in dichloromethane (30 mL) at -78° C. under a dry nitrogen atomosphere. The solution was allowed to warm to ambient temperature and was stirred for 4 h. The reaction mixture was quenched with water and partitioned between water and ether. Silica gel was added to the ether phase and the solvent was removed, The adsorbate was flash chromatographed (eluent 7:3 pet. ether:ethyl acetate) to provide the title compound as a white solid (2.08 g, 96%): mp: 197-199° C.; NMR (CDCl3); δ 8.28 (s, 1H), 7.92 (d, J=8 Hz, 1H), 7.59 (dm, J=8 Hz, 1H), 7.50 (ddd, J=8, 7, 1 Hz, 1H), 7.39-7.25 (m, 5H), 7.21 (d, J=2 Hz, 1H), 7.11 (d, J=9 Hz, 2H), 6.69 (d, J=9 Hz, 1H), 6.57 (dd, J=9, 2 Hz, 1H), 5.03 (s, 1H), 4.94 (s, 1H); MS (FAB+): 343 (15%, M+H); Anal. Calc. for C22H14O2S: C, 77.17, H, 4.12, N, 0:00. Found: C, 76.74, H, 4.04, N, 0.02.

Workup

  1. customThe reaction mixture was quenched with water
  2. custompartitioned between water and ether
  3. additionSilica gel was added to the ether phase
  4. customthe solvent was removed
  5. customchromatographed (eluent 7:3 pet. ether:ethyl acetate)

Sources & evidence

ORD record
ord-c489889073d24379ae4447d9f12549ec
Source dataset
uspto-grants-2000_08
Patent number
US06110962

Reaction notes

Loading…