Boron tribromide dichloromethane → HCID 23445616, compound

HRID 1067339Notes

Reaction equation

HRID 1067339 reaction equation
[Br:1][C:2]1[CH:31]=[CH:30][C:5]([CH2:6][C:7]2[O:8][C:9]([CH3:29])=[C:10]([CH3:28])[C:11]=2[C:12]([C:14]2[CH:19]=[C:18]([CH:20]([CH3:22])[CH3:21])[C:17]([O:23]C)=[C:16]([CH:25]([CH3:27])[CH3:26])[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:31]=[CH:30][C:5]([CH2:6][C:7]2[O:8][C:9]([CH3:29])=[C:10]([CH3:28])[C:11]=2[C:12]([C:14]2[CH:19]=[C:18]([CH:20]([CH3:22])[CH3:21])[C:17]([OH:23])=[C:16]([CH:25]([CH3:26])[CH3:27])[CH:15]=2)=[O:13])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 22277759Boron tribromide dichloromethaneHCID 23445618[2-(4-Bromo-benzyl)-4,5-dimethyl-furan-3-yl]-(3,5-diisopropyl-4-methoxy-phenyl)-methanone

Product 1

HCID 23445616HCID 23445616, compoundYield 88%

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]-(3,5-diisopropyl-4-methoxy-phenyl)-methanone (1.61 g, 3.32 mmol) and 1M boron tribromide/CH2Cl2 (6.97 mL) in CH2Cl2. Purification on Biotage KP-Sil eluting with 15% acetone/hexane gave 1.37 g (88%) of the title compound. 1H NMR (DMSO-d6) δ1.12 (d, 12H), 1.78 (s, 3H), 2.17 (s, 3H), 3.30 (septet, 2H), 3.81 (s, 2H), 7.01 (dd, 2H), 7.40 (s, 2H), 7.42 (d, 2H), 9.10 (s, 1H). IR (KBr) 3400, 2950, 1640, 1580 and 1310 cm−1. mass spectrum (EI) m/z 468 (M+). Anal. Calcd. for C26H29BrO3: C, 66.53; H, 6.23; N, 0.00. Found: C, 66.57; H, 6.39; N, 0.05.

Workup

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

Sources & evidence

ORD record
ord-1e9f9eebfb6c4c0e829283a201346305
Source dataset
uspto-grants-2001_06
Patent number
US06248764B1

Reaction notes

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