Boron tribromide → HCID 15481241, compound

HRID 1873131Notes

Reaction equation

HRID 1873131 reaction equation
C[O:2][C:3]1[CH:19]=[CH:18][C:17]2[C:5](=[CH:6][C:7]3[S:11][C:10]4[CH:12]=[CH:13][CH:14]=[CH:15][C:9]=4[C:8]=3[C:16]=2[C:20]2[CH:25]=[CH:24][C:23]([O:26]C)=[CH:22][CH:21]=2)[CH:4]=1.B(Br)(Br)Br>C(Cl)Cl>[OH:26][C:23]1[CH:24]=[CH:25][C:20]([C:16]2[C:8]3[C:9]4[CH:15]=[CH:14][CH:13]=[CH:12][C:10]=4[S:11][C:7]=3[CH:6]=[C:5]3[C:17]=2[CH:18]=[CH:19][C:3]([OH:2])=[CH:4]3)=[CH:21][CH:22]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 15481240HCID 15481240, compound

Product 1

HCID 15481241HCID 15481241, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a cold (-75° C.) solution of 8-methoxy-11-(4-methoxy-phenyl)-benzo[b]naphtho[2,3-d]thiophene (1.92 g, 5.18 mmol) in anhydrous methylene chloride was added a solution of boron tribromide (1 M in methylene chloride, 6.74 mL, 6.74 mmol, 1.3 eq) dropwise over a period of 18 minutes. After stirring in the cold for 3.5 hours and at ambient temperature for approximately 19 hours the reaction mixture was quenched with water (100 mL), diluted with methylene chloride (50 mL) and the organics were extracted with diethyl ether (1×100 mL, 1×75 mL). The extracts were combined, washed with brine, and combined with silica gel. The solvents were removed and the adsorbate was flash chromatographed (74/26 petrolem ether/ethyl acetate) and dried at 92° C. overnight to the title compound as an off-white solid (1.07 g, 91%): mp 233-235° C.; NMR (DMSO-d6); δ 9.91 (broad s, 1H), 9.77 (broad s, 1H), 8.30 (s, 1H), 7.88 (d, J=8 Hz, 1H), 7.40 (d, J=8 Hz, 1H), 7.35 (ddd, J=8, 8, 1 Hz, 1H), 7.23 (d, J=2 Hz, 1H), 7.15 (d, J=8 Hz, 2H), 7.09 (ddd, J=8, 8, 1 Hz, 1H), 7.06-7.00 (multiplet containing a doublet at 7.05, J=8 Hz, 3 H), 6.71 (d, J=8 Hz, 1H); MS (+FAB): [M+] 343; Anal. Calc. for C22H14O2S: C, 77.17, H, 4.12, N, 0.00. Found: C, 76.43, H, 3.82, N, 0.01.

Workup

  1. customat ambient temperature for approximately 19 hours the reaction mixture was quenched with water (100 mL)
  2. additiondiluted with methylene chloride (50 mL)
  3. extractionthe organics were extracted with diethyl ether (1×100 mL, 1×75 mL)
  4. washwashed with brine
  5. customThe solvents were removed
  6. customchromatographed (74/26 petrolem ether/ethyl acetate)
  7. dry with materialdried at 92° C. overnight to the title compound as an off-white solid (1.07 g, 91%)

Sources & evidence

ORD record
ord-6c311ee7880b4be880bae52cbecf0c5a
Source dataset
uspto-grants-2000_08
Patent number
US06110962

Reaction notes

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