Boron tribromide → HCID 22665460, compound

HRID 1954294Notes

Reaction equation

HRID 1954294 reaction equation
[CH2:1]([C:8]1[O:9][C:10]([CH3:28])=[C:11]([CH3:27])[C:12]=1[C:13]([C:15]1[CH:20]=[C:19]([CH2:21][CH3:22])[C:18]([O:23]C)=[C:17]([CH2:25][CH3:26])[CH:16]=1)=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.B(Br)(Br)Br.[K+].[Br-]>>[CH3:28][C:10]1[O:9][C:8]2[CH:1]=[C:2]3[C:7](=[C:13]([C:15]4[CH:16]=[C:17]([CH2:25][CH3:26])[C:18]([OH:23])=[C:19]([CH2:21][CH3:22])[CH:20]=4)[C:12]=2[C:11]=1[CH3:27])[CH:6]=[CH:5][CH:4]=[CH:3]3

Participants

4

Reactant 3

HCID 25134Boron tribromideHCID 253877Potassium BromideHCID 23445624HCID 23445624, compound

Product 1

HCID 22665460HCID 22665460, compound

Procedure

The title compound was prepared according to the procedure in Example 1, step 5, using (2-benzyl-4,5-dimethyl-furan-3-yl)-(3,5-diethyl-4-methoxy-phenyl)-methanone (22.0 g, 58.4 mmol) and boron tribromide (36.8 mL, 0.389 mol). Purification on Biotage KP-Sil, eluting with a 0, 2 & 5% EtOAc/hexane step gradient followed by trituration with hexane gave 1.34 g (8%), of the title compound as an off white solid. 1H NMR (DMSO-d6) δ 1.15 (t, 6 H), 1.59 (s, 3 H), 2.37 (s, 3 H), 2.59-2.72 (m, 4 H), 6.89 (s, 2 H), 7.29 (d of t, 1 H), 7.39 (d of t, 1 H), 7.56 (d, 1 H), 7.90 (s, 1 H), 7.96 (d, 1 H), 8.29 (s, 1 H). IR (KBr) 3540, 2960, 1475, 1180 and 1140 cm-1. mass spectrum (EI) m/z 344 (M+). Anal. Calcd. for C24H24O2.0.3H2O: C, 82.39; H, 7.09; N, 0.00. Found: C, 82.53; H, 7.11; N, 0.05.

Workup

  1. customThe title compound was prepared
  2. customPurification on Biotage KP-Sil
  3. washeluting with a 0, 2 & 5% EtOAc/hexane step gradient
  4. customgave 1.34 g (8%)

Sources & evidence

ORD record
ord-b17cae8d6e314c80a73783bc76a82cf3
Source dataset
uspto-grants-2000_09
Patent number
US06121271

Reaction notes

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