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

HRID 1280897Notes

Reaction equation

HRID 1280897 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:29]=[CH:30][CH:31]=1)[CH2:5][C:6]1[O:7][C:8]([CH3:28])=[C:9]([CH3:27])[C:10]=1[C:11]([C:13]1[CH:18]=[C:17]([CH:19]([CH3:21])[CH3:20])[C:16]([O:22]C)=[C:15]([CH:24]([CH3:26])[CH3:25])[CH:14]=1)=[O:12].B(Br)(Br)Br.C(Cl)Cl>C(Cl)Cl>[Br:1][C:2]1[CH:3]=[C:4]([CH:29]=[CH:30][CH:31]=1)[CH2:5][C:6]1[O:7][C:8]([CH3:28])=[C:9]([CH3:27])[C:10]=1[C:11]([C:13]1[CH:14]=[C:15]([CH:24]([CH3:26])[CH3:25])[C:16]([OH:22])=[C:17]([CH:19]([CH3:20])[CH3:21])[CH:18]=1)=[O:12]

Participants

4

Reactant 2

HCID 22277759Boron tribromide dichloromethaneHCID 23445630[2-(3-Bromo-benzyl)-4,5-dimethyl-furan-3-yl]-(3,5-diisopropyl-4-methoxy-phenyl)-methanone

Product 1

HCID 23445623[2-(3-Bromo-benzyl)-4,5-dimethyl-furan-3-yl]-(3,5-diisopropyl-4-hydroxy-phenyl)-methanoneYield 76.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The title compound was prepared according to the procedure in Example 5, step 3 using [2-(3-bromo-benzyl)-4,5-dimethyl-furan-3-yl]-(3,5-diisopropyl-4-methoxy-phenyl)-methanone (1.34 g, 2.78 mmol) and 1M boron tribromide/CH2Cl2 (5.84 mL) in CH2Cl2. Purification on Biotage KP-Sil eluting with 15% acetone/hexane gave 0.995 g (73%) of the title compound. 1H NMR (DMSO-d6) δ 1.14 (d, 12H), 1.80 (s, 3H), 2.19 (s, 3H), 3.32 (septet, 2H), 3.87 (s, 2H), 7.09 (d, 1H), 7.22 (t, 1H), 7.26 (s, 1H), 7.39 (d, 1H), 7.43 (s, 2H), 9.13 (s, 1H). IR (KBr) 3350, 2950, 1580, 1560 and 1325 cm−1. mass spectrum (EI) m/z 468 (M+). Anal. Calcd. for C26H29BrO3: C, 66.53; H, 6.23; N, 0.00. Found: C, 66.50; H, 6.22; N, 0.08.

Workup

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

Sources & evidence

ORD record
ord-3e4be3c54906436da0cfb9b93d2d54f1
Source dataset
uspto-grants-2002_09
Patent number
US06451845B1

Reaction notes

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