Bis(2-bromoethyl) ether → HCID 67975013, compound

HRID 1771456Notes

Reaction equation

[NH2:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][C:11]=1[C:12]1[CH:21]=[CH:20][C:19]2[C:14](=[CH:15][CH:16]=[C:17]([O:22][CH3:23])[CH:18]=2)[CH:13]=1)[C:5]([O:7][CH3:8])=[O:6].CCN(C(C)C)C(C)C.[CH2:33]([O:36][CH2:37][CH2:38]Br)[CH2:34]Br>C1(C)C=CC=CC=1>[CH3:23][O:22][C:17]1[CH:18]=[C:19]2[C:14](=[CH:15][CH:16]=1)[CH:13]=[C:12]([C:11]1[CH:10]=[CH:9][C:4]([C:5]([O:7][CH3:8])=[O:6])=[CH:3][C:2]=1[N:1]1[CH2:38][CH2:37][O:36][CH2:33][CH2:34]1)[CH:21]=[CH:20]2

Participants

Conditions

Temperature: 110 °C

Procedure

To a solution of methyl 3-amino-4-(6-methoxynaphthalen-2-yl)benzoate (1.00 g, 3.30 mmol) (see Step 1 of Example 5) and DIPEA (1.70 g, 13.2 mmol) in anhydrous toluene (20 mL) containing catalytic amount of KI (100 mg, 0.660 mmol) was added 2,2′-dibromodiethyl ether (1.50 g, 6.60 mmol). The mixture was heated to 110° C. for 3 days. The mixture was concentrated in vacuo and the residue was purified by column chromatography on silica gel (PE/EtOAc=10/1) to give the product (1.00 g, yield 81%).

Workup

concentrationThe mixture was concentrated in vacuo
customthe residue was purified by column chromatography on silica gel (PE/EtOAc=10/1)

Sources & evidence

ORD record: ord-44928d89cb5f48c2abf4c131c5ef4f21
Source dataset: uspto-grants-2016_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09249132B2

Reaction notes

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