1,3-Dibromopropane → HCID 70549889, compound

HRID 1702582Notes

Reaction equation

HRID 1702582 reaction equation
[CH2:1]([O:8][CH:9]1[CH:14]=[C:13]([OH:15])[CH:12]=[C:11]([O:16][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH:10]1[CH:24]=[CH:25][C:26]([C:28]1[CH:33]=[CH:32][C:31]([O:34][CH3:35])=[C:30]([O:36][CH2:37][C:38]2[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=2)[CH:29]=1)=[O:27])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([O-])([O-])=O.[K+].[K+].[Br:50][CH2:51][CH2:52][CH2:53]Br>CN(C=O)C>[CH2:17]([O:16][CH:11]1[CH:12]=[C:13]([O:15][CH2:53][CH2:52][CH2:51][Br:50])[CH:14]=[C:9]([O:8][CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[CH:10]1[CH:24]=[CH:25][C:26]([C:28]1[CH:33]=[CH:32][C:31]([O:34][CH3:35])=[C:30]([O:36][CH2:37][C:38]2[CH:39]=[CH:40][CH:41]=[CH:42][CH:43]=2)[CH:29]=1)=[O:27])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

5

Reactant 3

HCID 80011,3-DibromopropaneHCID 11430Potassium CarbonateHCID 70546782HCID 70546782, compound

Product 1

HCID 70549889HCID 70549889, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 2.37 g (5 mmol) of 2,3',6-tris(benzyloxy)-4-hydroxy-4'-methoxydihydrochalcone, 1.38 g (10 mmol) of K2CO3, and 70.1 g (50 mmol) of 1,3-dibromopropane in 75 mL of DMF was reacted for 48 hours, after which standard workup yielded 2.91 g (84%) of 2,3',6-tris(benzyloxy)-4-(3-bromopropoxy)-4'-methoxydihydrochalcone as a white solid. The resulting intermediate bromide (2.91 g, 4.18 mmol) was dissolved in 50 mL of P(OCH3)3 and refluxed for 39 hours. After all solvent was removed in vacuo, standard workup, followed by column chromatography over 200 g of silica gel (CHCl3 --CH3OH), yielded 1.93 g (64%) of 2.3',6-tris(benzyloxy)-4-(dimethyl-3-phosphopropoxy)-4'-methoxydihydrochalcone as an oil, which crystallized on standing. Crystallization from hexane-EtOAc yielded colorless clusters: mp 92°-95.5° C.; IR (film) 5.88 (C=O) μm; UV (MeOH)λmax 278 nm (ε 7600); NMR (CDCl3)δ 2.90 (m, 4H, ArCOCH2CH2Ar'), 3.64 [s, 6H, PO(OCH3)2 ], 3.77 (s, 3H, Ar'OCH3), 3.94 (t, 2H, J=6 Hz, ArOCH2), 5.03 (s, 6H, PhCH2O), 6.17 (s, 2H, ArH), 7.37 (s, 15H, PhH). Anal (C42H45O9P) C, H.

Workup

  1. customwas reacted for 48 hours

Sources & evidence

ORD record
ord-59b79b8404484a739faf9d3ecc49c9be
Source dataset
uspto-grants-1982_09
Patent number
US04348333

Reaction notes

Loading…