[2-(2-Bromo-benzyl)-4,5-dimethyl-furan-3-yl]-(3,5-diisopropyl-4-methoxy-phenyl)-methanone → [2-(2-Bromo-benzyl)-4,5-dimethyl-furan-3-yl]-(3,5-diisopropyl-4-hydroxy-phenyl)-methanone

HRID 1067331Notes

Reaction equation

HRID 1067331 reaction equation
[Br:1][C:2]1[CH:31]=[CH:30][CH:29]=[CH:28][C:3]=1[CH2:4][C:5]1[O:6][C:7]([CH3:27])=[C:8]([CH3:26])[C:9]=1[C:10]([C:12]1[CH:17]=[C:16]([CH:18]([CH3:20])[CH3:19])[C:15]([O:21]C)=[C:14]([CH:23]([CH3:25])[CH3:24])[CH:13]=1)=[O:11].B(Br)(Br)Br.C(Cl)Cl>C(Cl)Cl>[Br:1][C:2]1[CH:31]=[CH:30][CH:29]=[CH:28][C:3]=1[CH2:4][C:5]1[O:6][C:7]([CH3:27])=[C:8]([CH3:26])[C:9]=1[C:10]([C:12]1[CH:17]=[C:16]([CH:18]([CH3:19])[CH3:20])[C:15]([OH:21])=[C:14]([CH:23]([CH3:24])[CH3:25])[CH:13]=1)=[O:11]

Participants

4

Reactant 2

HCID 12093942[2-(2-Bromo-benzyl)-4,5-dimethyl-furan-3-yl]-(3,5-diisopropyl-4-methoxy-phenyl)-methanoneHCID 22277759Boron tribromide dichloromethane

Product 1

HCID 12093943[2-(2-Bromo-benzyl)-4,5-dimethyl-furan-3-yl]-(3,5-diisopropyl-4-hydroxy-phenyl)-methanoneYield 72%

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]-(3,5-diisopropyl-4-methoxy-phenyl)-methanone (0.973 g, 2.01 mmol) and 1M boron tribromide/CH2Cl2 (4.23 mL) in CH2Cl2. Purification on Biotage KP-Sil eluting with 15% acetone/hexane gave 0.679 g (72%) of the title compound. 1H NMR (DMSO-d6) δ1.13 (d, 12H), 1.82 (s, 3H), 2.18 (s, 3H), 3.31 (septet, 2H), 3.94 (s, 2H), 7.12-7.17 (m, 2H), 7.30 (dt, 1H), 7.42 (s, 2H), 7.52 (d, 1H), 9.10 (s, 1H).

Workup

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

Sources & evidence

ORD record
ord-5ecbe7a783b2489a821030503cb96de6
Source dataset
uspto-grants-2001_06
Patent number
US06248764B1

Reaction notes

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