Boron tribromide dichloromethane → [2-(2-Bromo-benzyl)-4,5-dimethyl-furan-3-yl]-(3-cyclopentyl-4-hydroxy-phenyl)-methanone

HRID 1280930Notes

Reaction equation

HRID 1280930 reaction equation
[Br:1][C:2]1[CH:30]=[CH:29][CH:28]=[CH:27][C:3]=1[CH2:4][C:5]1[O:6][C:7]([CH3:26])=[C:8]([CH3:25])[C:9]=1[C:10]([C:12]1[CH:17]=[CH:16][C:15]([O:18]C)=[C:14]([CH:20]2[CH2:24][CH2:23][CH2:22][CH2:21]2)[CH:13]=1)=[O:11].B(Br)(Br)Br.C(Cl)Cl>C(Cl)Cl>[Br:1][C:2]1[CH:30]=[CH:29][CH:28]=[CH:27][C:3]=1[CH2:4][C:5]1[O:6][C:7]([CH3:26])=[C:8]([CH3:25])[C:9]=1[C:10]([C:12]1[CH:17]=[CH:16][C:15]([OH:18])=[C:14]([CH:20]2[CH2:24][CH2:23][CH2:22][CH2:21]2)[CH:13]=1)=[O:11]

Participants

4

Reactant 2

HCID 22277759Boron tribromide dichloromethaneHCID 23445625[2-(2-Bromo-benzyl)-4,5-dimethyl-furan-3-yl]-(3-cyclopentyl4-methoxy-phenyl)-methanone

Product 1

HCID 23445646[2-(2-Bromo-benzyl)-4,5-dimethyl-furan-3-yl]-(3-cyclopentyl-4-hydroxy-phenyl)-methanoneYield 50%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The title compound was prepared according to the procedure in Example 5, step 3 using [2-(2-bromo-benzyl)-4,5-dimethyl-furan-3-yl]-(3-cyclopentyl-4-methoxy-phenyl)-methanone (2.82 g, 6.03 mmol) and 1M boron tribromide/CH2Cl2 (18.7 mL) in CH2Cl2. Purification on Biotage KP-Sil eluting with a 2, 5 & 10% EtOAc/pet. ether step gradient gave 1.36 g (50%) of the title compound. (DMSO-d6) δ 1.42-1.44 (m, 2H), 1.58-1.72 (m, 4H), 1.79 (s, 3H), 1.87-1.92 (m, 2H), 2.16 (s, 3H), 3.17 (quintet, 1H), 3.92 (s, 2H), 6.85 (d, 1H), 7.12-7.17 (m, 2H), 7.29 (t, 1H), 7.45 (dd, 1H), 7.50-7.52 (m, 2H), 10.31 (s, 1H).

Workup

  1. customThe title compound was prepared
  2. customPurification on Biotage KP-Sil
  3. washeluting with a 2, 5 & 10% EtOAc/pet. ether step gradient

Sources & evidence

ORD record
ord-dfc8e8eb446648f09508c953ad01efcf
Source dataset
uspto-grants-2002_09
Patent number
US06451845B1

Reaction notes

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