Boron tribromide → 4-Benzo[b]naphtho[2,3-d]thiophen-11-yl-phenol

HRID 1873128Notes

Reaction equation

HRID 1873128 reaction equation
B(Br)(Br)Br.[CH2:5]([C:12]1[S:16][C:15]2[CH:17]=[CH:18][CH:19]=[CH:20][C:14]=2[C:13]=1[C:21]([C:23]1[CH:28]=[CH:27][C:26]([O:29]C)=[CH:25][CH:24]=1)=O)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1>ClCCl>[CH:20]1[C:14]2[C:13]3[C:21]([C:23]4[CH:28]=[CH:27][C:26]([OH:29])=[CH:25][CH:24]=4)=[C:11]4[C:6](=[CH:5][C:12]=3[S:16][C:15]=2[CH:17]=[CH:18][CH:19]=1)[CH:7]=[CH:8][CH:9]=[CH:10]4

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 10808337HCID 10808337, compound

Product 1

HCID 107823884-Benzo[b]naphtho[2,3-d]thiophen-11-yl-phenolYield 73.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A 1.0 M solution of boron tribromide in dichloromethane (130 mL, 130 mmol) was added slowly to a stirrred solution of (2-benzyl-benzo[b]thiophen-3-yl)-(4-methoxy-phenyl)-methanone (14.5 g, 40.45 mmol) in dichloromethane (130 mL) at -78° C. under a dry nitrogen atomosphere. The solution was allowed to warm to ambient temperature and was stirred overnight. The reaction mixture was quenched with water and partitioned between water and dichloromethane. Silica gel was added to the dichloromethane phase and the solvent was removed, The adsorbate was flash chromatographed (eluent 4:1 pet. ether:ethyl acetate) to provide a white solid (9.75 g). This solid was recrystalized from acetic acid to provide off-white needles (8.78, 56%): mp: 112-116° C.; NMR (CDCl3); δ 8.33 (s, 1H), 7.94 (dt, J=8 Hz, 1H), 7.77 (dm, J=8 Hz, 1H), 7.64 (dm, J=8 Hz, 1H), 7.52 (ddd, J=8, 7, 1 Hz, 1H), 7.37 (m, 2H), 7.29 (d, J=9 Hz, 2H), 7.11 (d, J=9 Hz, 2H), 7.08 (m, 1H), 6.85 (dm, J=8 Hz, 1H), 2.11 (s, 3H, acetic acid CH3); MS (EI): 326 (100%, MI); Anal. Calc. for C22H14OS.C2H4O2: C, 74.59, H, 4.69, N, 0.00. Found: C, 74.40, H, 4.59, N, 0.15.

Workup

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

Sources & evidence

ORD record
ord-22f721cf8aac4b47b8007ebf26f18e63
Source dataset
uspto-grants-2000_08
Patent number
US06110962

Reaction notes

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