Bis(Chloromethyl) Ether → HCID 21274990, compound

HRID 1382639Notes

Reaction equation

[C:1]1([CH:7]([C:21]2[CH:26]=[CH:25][C:24]([F:27])=[CH:23][CH:22]=2)[CH:8]([C:13]2[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][CH:14]=2)[C:9]([F:12])([F:11])[F:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl.N1C=CC=CC=1.C1(C(C2C=CC(F)=CC=2)C(C2C=C[C:50]([OH:53])=CC=2)C(F)(F)F)C=CC=CC=1.ClCOCCl.[OH-].[Na+]>C1C=CC=CC=1>[C:1]1([CH:7]([C:21]2[CH:26]=[CH:25][C:24]([F:27])=[CH:23][CH:22]=2)[CH:8]([C:13]2[CH:18]=[CH:17][C:16]([O:19][CH2:20][O:53][CH3:50])=[CH:15][CH:14]=2)[C:9]([F:12])([F:11])[F:10])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

Conditions

Temperature: 200 °C

Procedure

A mixture of 18.72 g (50 mmoles) of 1-phenyl-3,3,3-trifluoro-1-(4-fluorophenyl)-2-(4-methoxyphenyl)-propane, prepared as described in Example 19, and 56 g of pyridine hydrochloride is heated at 200° C. for 3 hours, and then processed as described in Example 1. The resulting crude 1-phenyl-3,3,3-trifluoro-1-(4-fluorophenyl)-2-(4-hydroxyphenyl)-propane is dissolved in 70 ml of benzene, then 6.44 g (80 mmoles) of chloromethylether and 6 g (300 mmoles) of powdered sodium hydroxide are added, and the mixture is boiled for one hour. The reaction mixture is diluted with 100 ml of benzene, washed until neutral with a 20% aqueous ammonium chloride solution, dried and evaporated. The residue is crystallized from isopropanol. 12.54 g (62%) of 1-phenyl-3,3,3-trifluoro-1-(4-fluorophenyl)-2-[4-(methoxy-methoxy)-phenyl]-propane are obtained; m.p.: 96.5°-99° C.

Workup

customprepared
washwashed until neutral with a 20% aqueous ammonium chloride solution
customdried
customevaporated
customThe residue is crystallized from isopropanol

Sources & evidence

ORD record: ord-cc092208381a440fa317edbb88d740f5
Source dataset: uspto-grants-1989_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04806685

Reaction notes

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