Boron tribromide → HCID 70014505, compound

HRID 1416980Notes

Reaction equation

O.C[O:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[CH:19]=[CH:18][C:17]3[C:12](=[CH:13][CH:14]=[C:15]([O:20]C)[CH:16]=3)[C:11]=2[O:22][C:23]2[CH:28]=[CH:27][C:26]([CH:29]=[CH:30][C:31]([OH:33])=[O:32])=[CH:25][CH:24]=2)=[CH:6][CH:5]=1.B(Br)(Br)Br>ClCCl>[OH:3][C:4]1[CH:5]=[CH:6][C:7]([C:10]2[CH:19]=[CH:18][C:17]3[C:12](=[CH:13][CH:14]=[C:15]([OH:20])[CH:16]=3)[C:11]=2[O:22][C:23]2[CH:28]=[CH:27][C:26]([CH:29]=[CH:30][C:31]([OH:33])=[O:32])=[CH:25][CH:24]=2)=[CH:8][CH:9]=1

Participants

Conditions

Temperature: 5 °C

Procedure

A solution was prepared of 658 mg (1.54 mmol) of 3-[4-((2-(4-methoxyphenyl)-6-methoxynaphth-1-yl)oxy)phenyl]propenoic acid hydrate in 10 mL of dichloromethane. The solution was cooled to 5° C. and 0.44 mL (4.7 mmol) of BBr3 was added. The reaction was allowed to proceed for one hour at 0° C. under a nitrogen atmosphere. The reaction was quenched by pouring into water and extracting three times with ethyl acetate. The combined ethyl acetate extracts were washed with water, brine, dried with Na2SO4, and evaporated to an oily, red solid. The product was purified by chromatography on a silica gel column eluted with MeOH--CHCl3 (1:99) (v/v). This yielded 489 mg of the title compound as a yellow, amorphous solid, mp 150-153° C.

Workup

customThe reaction was quenched
additionby pouring into water
extractionextracting three times with ethyl acetate
washThe combined ethyl acetate extracts were washed with water, brine
dry with materialdried with Na2SO4
customevaporated to an oily, red solid
customThe product was purified by chromatography on a silica gel column
washeluted with MeOH--CHCl3 (1:99) (v/v)

Sources & evidence

ORD record: ord-7195dfa1d01a4154b758e67a5597dda9
Source dataset: uspto-grants-1999_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05916916

Reaction notes

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