Boron tribromide → HCID 59770047, compound

HRID 2218635Notes

Reaction equation

HRID 2218635 reaction equation
[CH:1]1[C:11]2[CH2:10][CH2:9][C:8]3[CH:12]=[CH:13][CH:14]=[CH:15][C:7]=3[C:6](=[CH:16][C:17]3[CH:18]=[CH:19][C:20]([O:28]C)=[C:21]([NH:23][S:24]([CH3:27])(=[O:26])=[O:25])[CH:22]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1.B(Br)(Br)Br.C([O-])(O)=O.[Na+]>C(Cl)Cl>[CH:1]1[C:11]2[CH2:10][CH2:9][C:8]3[CH:12]=[CH:13][CH:14]=[CH:15][C:7]=3[C:6](=[CH:16][C:17]3[CH:18]=[CH:19][C:20]([OH:28])=[C:21]([NH:23][S:24]([CH3:27])(=[O:26])=[O:25])[CH:22]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 25134Boron tribromide2×HCID 516892Sodium BicarbonateHCID 59770016HCID 59770016, compound

Product 1

HCID 59770047HCID 59770047, compoundYield 97.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Cool a solution of N-[5-(10,11-dihydro-dibenzo[a,d]cyclohepten-5-ylidenemethyl)-2-methoxy-phenyl]-methanesulfonamide (100 mg, 0.247 mmol) in CH2Cl2 (5 mL) to 0° C. Add 23.3□L (62 mg, 0.247 mmol) BBr3 and warm up to room temperature. Stir for 20 min, then add 30.0□L (79.5 mg, 0.317 mmol) more BBr3. Stir at room temperature for 1 h, then dilute reaction with 90 mL saturated aqueous NaHCO3. Stir overnight. Separate the layers, and extract the aqueous layer with CH2Cl2. Combine and dry organics (MgSO4), filter, and concentrate to afford 94 mg (97%) of a white foam, mp 122.6° C. 1H NMR (CDCl3) δ 2.70 (s, 3H), 2.79-3.59 (br m, 4H), 5.94 (s, 1H), 6.39 (s, 1H), 6.70-7.98 (m, 12H); MS (ES) 414 (M+Na), 390 (M−H). HPLC shows 99% purity.

Workup

  1. additionAdd
  2. stirringStir at room temperature for 1 h
  3. additiondilute
  4. stirringStir overnight
  5. customSeparate the layers
  6. extractionextract the aqueous layer with CH2Cl2
  7. filtrationCombine and dry organics (MgSO4), filter
  8. concentrationconcentrate

Sources & evidence

ORD record
ord-61835a76f16e431a86a15b60a5d9f5e6
Source dataset
uspto-grants-2008_08
Patent number
US07411072B2

Reaction notes

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