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

HRID 1067334Notes

Reaction equation

HRID 1067334 reaction equation
[CH:1]([C:4]1[CH:5]=[C:6]([CH:10]=[C:11]([CH:15]([CH3:17])[CH3:16])[C:12]=1[O:13][CH3:14])[C:7]([OH:9])=O)([CH3:3])[CH3:2].C(Cl)(=O)C(Cl)=O.[Sn](Cl)(Cl)(Cl)Cl.[Br:29][C:30]1[CH:31]=[C:32]([CH:41]=[CH:42][CH:43]=1)[CH2:33][C:34]1[O:35][C:36]([CH3:40])=[C:37]([CH3:39])[CH:38]=1>CN(C)C=O.C(Cl)Cl>[Br:29][C:30]1[CH:31]=[C:32]([CH:41]=[CH:42][CH:43]=1)[CH2:33][C:34]1[O:35][C:36]([CH3:40])=[C:37]([CH3:39])[C:38]=1[C:7]([C:6]1[CH:10]=[C:11]([CH:15]([CH3:17])[CH3:16])[C:12]([O:13][CH3:14])=[C:4]([CH:1]([CH3:2])[CH3:3])[CH:5]=1)=[O:9]

Participants

7

Reactant 4

HCID 24287Tin tetrachlorideHCID 65578Oxalyl chlorideHCID 15895030HCID 15895030, compoundHCID 234456292-(3-Bromo-benzyl)4,5-dimethyl-furan

Product 1

HCID 23445630[2-(3-Bromo-benzyl)-4,5-dimethyl-furan-3-yl]-(3,5-diisopropyl-4-methoxy-phenyl)-methanoneYield 65.1%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent

Procedure

The title compound was prepared according to the procedure in Example 5, step 2 using 3,5-diisopropyl-p-anisic acid (1.02 g, 4.32 mmol, RN-117439-59-5), oxalyl chloride (0.415 mL, 4.75 mmol), N,N-dimethylformamide (2 drops), tin (IV) chloride (0.556 mL, 4.75 mmol) and 2-(3-bromo-benzyl)-4,5-dimethyl-furan (1.15 g, 4.32 mmol) in CH2Cl2. Purification on Biotage KP-Sil eluting with 3% EtOAc/pet. ether gave 1.36 g (65%) of the title compound as a yellow clear oil. 1H NMR (DMSO-d6) δ1.17 (d, 12H), 1.80 (s, 3H), 2.20 (s, 3H), 3.28 (septet, 2H), 3.74 (s, 3H), 3.87 (s, 2H), 7.06 (d, 1H), 7.19 (d, 1H), 7.24 (s, 1H), 7.38 (dd, 1H), 7.46 (s, 2H).

Workup

  1. customThe title compound was prepared
  2. customPurification on Biotage KP-Sil
  3. washeluting with 3% EtOAc/pet. ether

Sources & evidence

ORD record
ord-e6f488b3fd7146aa9f2245828ed32671
Source dataset
uspto-grants-2001_06
Patent number
US06248764B1

Reaction notes

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