3-Bromoanisole → HCID 15859360, compound

HRID 849673Notes

Reaction equation

[Mg].Br[C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([O:9][CH3:10])[CH:4]=1.[CH3:11][N:12]([CH2:14][CH:15]1[C:24](=[O:25])[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[S:17][CH2:16]1)[CH3:13].[Cl-].[NH4+]>O1CCCC1>[CH3:13][N:12]([CH2:14][CH:15]1[C:24]([C:3]2[CH:8]=[CH:7][CH:6]=[C:5]([O:9][CH3:10])[CH:4]=2)([OH:25])[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[S:17][CH2:16]1)[CH3:11]

Participants

Conditions

Temperature: 20 °C

Procedure

The corresponding Grignard reagent was prepared from 0.73 g magnesium turnings and 5.61 g 1-bromo-3-methoxy-benzene in 20 ml of dry tetrahydrofuran, with gentle boiling. A solution of 4.43 g (RS)-3-dimethylaminomethyl-thiochroman-4-one in 10 ml dry tetrahydrofuran was added drop-wise thereto at +5 to 10° C. The batch was subsequently stirred for 6 hours at 20° C. and was then decomposed with 10 ml of a saturated ammonium chloride solution. The batch was extracted three times with diethyl ether, and the combined extracts were washed with a saturated sodium chloride solution and dried over sodium sulphate. The crude product which remained after evaporating off the volatile constituents was purified by column chromatography using ethyl acetate as the elutant, whereupon 3.68 g (55.8% theoretical) of the title compound was obtained.

Workup

customat +5 to 10° C
extractionThe batch was extracted three times with diethyl ether
washthe combined extracts were washed with a saturated sodium chloride solution
dry with materialdried over sodium sulphate
customafter evaporating off the volatile constituents
customwas purified by column chromatography

Sources & evidence

ORD record: ord-2bb7902850c243419c35e0eeca3eae73
Source dataset: uspto-grants-2000_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06013809

Reaction notes

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