Boron tribromide dichloromethane → [2-(4-Bromo-benzyl)-4,5-dimethyl-furan-3-yl]-(3-cyclopentyl4-hydroxy-phenyl)-methanone

HRID 1871318Notes

Reaction equation

HRID 1871318 reaction equation
[Br:1][C:2]1[CH:30]=[CH:29][C:5]([CH2:6][C:7]2[O:8][C:9]([CH3:28])=[C:10]([CH3:27])[C:11]=2[C:12]([C:14]2[CH:19]=[CH:18][C:17]([O:20]C)=[C:16]([CH:22]3[CH2:26][CH2:25][CH2:24][CH2:23]3)[CH:15]=2)=[O:13])=[CH:4][CH:3]=1.B(Br)(Br)Br.C(Cl)Cl>C(Cl)Cl>[Br:1][C:2]1[CH:30]=[CH:29][C:5]([CH2:6][C:7]2[O:8][C:9]([CH3:28])=[C:10]([CH3:27])[C:11]=2[C:12]([C:14]2[CH:19]=[CH:18][C:17]([OH:20])=[C:16]([CH:22]3[CH2:26][CH2:25][CH2:24][CH2:23]3)[CH:15]=2)=[O:13])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 22277759Boron tribromide dichloromethaneHCID 23445643[2-(4-Bromo-benzyl)-4,5-dimethyl-furan-3-yl]-(3-cyclopentyl-4-methoxy-phenyl)-methanone

Product 1

HCID 23445642[2-(4-Bromo-benzyl)-4,5-dimethyl-furan-3-yl]-(3-cyclopentyl4-hydroxy-phenyl)-methanoneYield 51%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The title compound was prepared according to the procedure in Example 5, step 3 using [2-(4-bromo-benzyl)-4,5-dimethyl-furan-3-yl]-(3-cyclopentyl-4-methoxy-phenyl)-methanone (3.38 g, 7.23 mmol) and 1M boron tribromide/CH2Cl2 (15.2 mL) in CH2Cl2. Purification on Biotage KP-Sil eluting with 15% acetone/hexane gave 1.66 g (51%) of the title compound. 1H NMR (DMSO-d6) δ 1.39-1.48 (m, 2 H), 1.59-1.65 (m, 2 H), 1.68-1.76 (m, 2 H), 1.79 (s, 3 H), 1.88-1.95 (m, 2 H), 2.18 (s, 3 H), 3.18 (quintet, 1 H), 3.81 (s, 2 H), 6.87 (d, 1 H), 7.04 (d, 2 H), 7.43-7.47 (m, 3 H), 7.53 (s, 1 H), 10.35 (s, 1 H). IR (KBr) 3300, 2950, 1650, 1575 and 1280 cm-1. mass spectrum (+ESI) m/z 453 (M+H). Anal. Calcd. for C25H25BrO3 : C, 66.23; H, 5.56; N, 0.00. Found: C, 66.12; H, 5.49; N, 0.03.

Workup

  1. customThe title compound was prepared
  2. customPurification on Biotage KP-Sil
  3. washeluting with 15% acetone/hexane

Sources & evidence

ORD record
ord-80177d17436a449d97ad42a3b0cc183a
Source dataset
uspto-grants-2000_08
Patent number
US06103708

Reaction notes

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