Bromide ion → HCID 15617528, compound

HRID 1087351Notes

Reaction equation

[Br-].[Cl-].C([Al+]CC)C.[F:8][C:9]([F:33])([F:32])[C:10]1[CH:11]=[C:12]([S:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][C:24]2[CH:31]=[CH:30][CH:29]=[CH:28][C:25]=2[CH:26]=[O:27])[CH:13]=[CH:14][CH:15]=1.Br[CH2:35][C:36]([O:38][C:39]([CH3:42])([CH3:41])[CH3:40])=[O:37]>O1CCCC1.CCCCCC.[Zn]>[OH:27][CH:26]([C:25]1[CH:28]=[CH:29][CH:30]=[CH:31][C:24]=1[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][S:16][C:12]1[CH:13]=[CH:14][CH:15]=[C:10]([C:9]([F:32])([F:8])[F:33])[CH:11]=1)[CH2:35][C:36]([O:38][C:39]([CH3:42])([CH3:41])[CH3:40])=[O:37]

Participants

Conditions

Temperature: 25 °C

Procedure

To a suspension of zinc dust (0.25 g, 3 mmoles) and cooper (I) bromide (0.02 g, 0.129 mmoles) in distilled tetrahydrofuran (20 ml) was added a solution of diethylaluminum chloride (2.8 ml, 2.8 mmoles) in hexane while stirring under argon at 25° C. The resulting mixture was cooled to -20° C., and a solution of 2-[7-(3-trifluoromethylphenylthio)heptyl]benzaldehyde (1.08 g, 2.8 mmoles) and t-butyl bromoacetate (0.42 ml, 2.8 mmoles) in tetrahydrofuran (6 ml) was added slowly at -20° C. The reaction mixture was permitted to warm to room temperature. After 2 hours the zinc was filtered off and washed with ether. The solvents were evaporated and the residue flash chroma-tographed on silica gel, eluted with 10% ethyl acetate in hexane, to provide the desired product.

Workup

temperatureThe resulting mixture was cooled to -20° C.
temperatureto warm to room temperature
filtrationAfter 2 hours the zinc was filtered off
washwashed with ether
customThe solvents were evaporated
washthe residue flash chroma-tographed on silica gel, eluted with 10% ethyl acetate in hexane

Sources & evidence

ORD record: ord-89ec2eec1a5d4663a8d9cf05e0d94faa
Source dataset: uspto-grants-1991_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05034537

Reaction notes

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