alpha-Bromo-o-fluorotoluene → Ethyl (2-chloro-5-(4-(((2-fluorobenzyl)(2-methyl-3-nitrophenyl)amino)methyl)phenoxy)phenoxy)acetate

HRID 1370973Notes

Reaction equation

[Cl:1][C:2]1[CH:14]=[CH:13][C:12]([O:15][C:16]2[CH:21]=[CH:20][C:19]([CH2:22][NH:23][C:24]3[CH:29]=[CH:28][CH:27]=[C:26]([N+:30]([O-:32])=[O:31])[C:25]=3[CH3:33])=[CH:18][CH:17]=2)=[CH:11][C:3]=1[O:4][CH2:5][C:6]([O:8][CH2:9][CH3:10])=[O:7].CCN(C(C)C)C(C)C.Br[CH2:44][C:45]1[CH:50]=[CH:49][CH:48]=[CH:47][C:46]=1[F:51]>CN(C)C=O.CCOCC>[Cl:1][C:2]1[CH:14]=[CH:13][C:12]([O:15][C:16]2[CH:17]=[CH:18][C:19]([CH2:22][N:23]([CH2:44][C:45]3[CH:50]=[CH:49][CH:48]=[CH:47][C:46]=3[F:51])[C:24]3[CH:29]=[CH:28][CH:27]=[C:26]([N+:30]([O-:32])=[O:31])[C:25]=3[CH3:33])=[CH:20][CH:21]=2)=[CH:11][C:3]=1[O:4][CH2:5][C:6]([O:8][CH2:9][CH3:10])=[O:7]

Participants

Conditions

Temperature: 90 °C

Procedure

The product from Example 306A (86 mg, 0.18 mmoles) in anhydrous dimethylformamide (1 mL) was treated with Hunig's base (0.107 mL, 0.5 mmoles) and 1-(bromomethyl)-2-fluorobenzene (0.198 mL, 0.9 mmoles) in anhydrous dimethylformamide (1 mL) and heated at 90° C. for 72 hours. The reaction was diluted with ether, washed with saturated NH4Cl, water, brine, dried (Na2SO4), filtered, and filtrate concentrated under reduced pressure. The residue purified by using ethyl acetate and hexane gradient on 10 g silica column to provide the title compound.

Workup

washwashed with saturated NH4Cl, water, brine
dry with materialdried (Na2SO4)
filtrationfiltered
concentrationfiltrate concentrated under reduced pressure
customThe residue purified

Sources & evidence

ORD record: ord-bef470ae371b40938e2750ee2dc6ad19
Source dataset: uspto-grants-2003_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06583180B2

Reaction notes

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