Boron tribromide dichloromethane → HCID 23445633, compound

HRID 1067362Notes

Reaction equation

HRID 1067362 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:14])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.B(Br)(Br)Br.C(Cl)Cl>C(Cl)Cl>[CH2:1]([C:8]1[O:9][C:10]([CH3:28])=[C:11]([CH3:27])[C:12]=1[C:13]([C:15]1[CH:16]=[C:17]([CH2:25][CH3:26])[C:18]([OH:23])=[C:19]([CH2:21][CH3:22])[CH:20]=1)=[O:14])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 22277759Boron tribromide dichloromethaneHCID 23445624HCID 23445624, compound

Product 1

HCID 23445633HCID 23445633, compoundYield 38.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The title compound was prepared according to the procedure in Example 5, step 3 using (2-benzyl-4,5-dimethyl-furan-3-yl)-(3,5-diethyl-4-methoxy-phenyl)-methanone (19.3 g, 51.2 mmol) and 1M boron tribromide/CH2Cl2 (36.8 mL) in CH2Cl2. Purification on Biotage KP-Sil eluting with a 2 & 5% EtOAc/hexane step gradient gave 7.07 g (37%) of the title compound. 1H NMR (DMSO-d6) δ1.08 (t, 6H), 1.79 (s, 3H), 2.17 (s, 3H), 2.57 (q, 4H), 3.81 (s, 2H), 7.06 (dd, 2H), 7.16-7.18 (m, 1H), 7.22-7.26 (m, 2H), 7.37 (s, 2H), 9.10 (s, 1H). mass spectrum (EI), m/z 362 (M+).

Workup

  1. customThe title compound was prepared
  2. customPurification on Biotage KP-Sil
  3. washeluting with a 2 & 5% EtOAc/hexane step gradient

Sources & evidence

ORD record
ord-11742f20edae41a4a4cfb1c75ef1e599
Source dataset
uspto-grants-2001_06
Patent number
US06248764B1

Reaction notes

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