Carbon Dioxide → HCID 18687862, compound

HRID 1873219Notes

Reaction equation

HRID 1873219 reaction equation
C(=O)=O.C(O)(C)C.[CH2:8]([C:15]1[O:16][C:17]2[CH:35]=[CH:34][CH:33]=[CH:32][C:18]=2[C:19]=1[C:20]([C:22]1[CH:27]=[CH:26][C:25]([O:28]C)=[CH:24][C:23]=1[O:30]C)=O)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.B(Br)(Br)Br>C(Cl)Cl>[CH:32]1[C:18]2[C:19]3[C:20]([C:22]4[CH:27]=[CH:26][C:25]([OH:28])=[CH:24][C:23]=4[OH:30])=[C:10]4[C:9](=[CH:8][C:15]=3[O:16][C:17]=2[CH:35]=[CH:34][CH:33]=1)[CH:14]=[CH:13][CH:12]=[CH:11]4

Participants

6

Reactant 4

HCID 280Carbon DioxideHCID 3776IsopropanolHCID 25134Boron tribromideHCID 18687870HCID 18687870, compound

Product 1

HCID 18687862HCID 18687862, compoundYield 38.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a cold (-76° C. dry ice, isopropanol bath) solution of (2-benzyl-benzofuran-3-yl)-(2,4-dimethoxy-phenyl)-methanone (6.13 g, 16.5 mmol) in anhydrous methylene chloride (60 mL) was added a 1 M solution of boron tribromide in methylene chloride (100 mL, 100 mmol, 6.06 eq) dropwise over a period of 20 minutes under a dry nitrogen atmosphere. The dry ice bath was removed and the reaction mixture was stirred at ambient temperature for 45 hours. After cooling in an ice bath water was carefully added and after quenching the reaction mixture was further diluted with water (300 mL). The organics were extracted with diethyl ether and methylene chloride. The extracts were combined, washed with water and brine, and combined with silica gel. The solvents were removed and the adsorbate was flash chromatographed (80/20 petroleum ether/ethyl acetate) to provide the title compound as a white solid (2.07 g, 38%): mp 201 -202° C.; NMR (CDCl3); δ8.03 (ddd, J=8, 7, 1 1 H), 8.01 (s, 1 H), 7.82 - 7.79 (m, 1 H), 7.58 - 7.54 (m, 2 H), 7.48 - 7.43 (m, 2 H), 7.20 (d, J=8 Hz, 1 H), 7.18 - 7.15 (m, 2 H), 6.70 (m, 2 H), 5.00 (s, 1 H), 4.70 (s, 1 H); Hi Res MS, Calc. Sample Mass for C22H14O3, 326.0942951, Measured Mass 326.09019, mas deviation 4 mmu. Anal. Calc. for C22H14O3: C, 80.97, H, 4.32, N, 0.00. Found: C, 79.80, H, 4.10, N, 0.07.

Workup

  1. customThe dry ice bath was removed
  2. temperatureAfter cooling in an ice bath water
  3. additionwas carefully added
  4. customafter quenching the reaction mixture
  5. additionwas further diluted with water (300 mL)
  6. extractionThe organics were extracted with diethyl ether and methylene chloride
  7. washwashed with water and brine
  8. customThe solvents were removed
  9. customchromatographed (80/20 petroleum ether/ethyl acetate)

Sources & evidence

ORD record
ord-4e9ddbf4ba744e618ea077ae6fe2e0b0
Source dataset
uspto-grants-2000_08
Patent number
US06110962

Reaction notes

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