1-(Bromomethyl)-4-chlorobenzene → HCID 21867552, compound

HRID 857327Notes

Reaction equation

[CH3:1][S:2][C:3]1[C:4]2[C:5](Br)=[CH:6][N:7]([Si:12]([CH:19]([CH3:21])[CH3:20])([CH:16]([CH3:18])[CH3:17])[CH:13]([CH3:15])[CH3:14])[C:8]=2[CH:9]=[CH:10][CH:11]=1.[Li]C(C)(C)C.[Cl:28][C:29]1[CH:36]=[CH:35][C:32]([CH2:33]Br)=[CH:31][CH:30]=1>CCOCC>[CH3:1][S:2][C:3]1[C:4]2[C:5]([CH2:33][C:32]3[CH:35]=[CH:36][C:29]([Cl:28])=[CH:30][CH:31]=3)=[CH:6][N:7]([Si:12]([CH:19]([CH3:21])[CH3:20])([CH:16]([CH3:18])[CH3:17])[CH:13]([CH3:15])[CH3:14])[C:8]=2[CH:9]=[CH:10][CH:11]=1

Participants

Conditions

Temperature: -78 °C

Procedure

To a solution of the indole of Step 4 (2.4 g, 6 mmol) in Et2O (50 mL) at −78° C. was added t-BuLi (7 mL, 12 mmol). The reaction mixture was stirred for 10 minutes at −78° C. and p-chlorobenzyl bromide (3.6 g, 18 mmol) was added. The reaction mixture was stirred for 2 hours at r.t. and was quenched with saturated aqueous NH4Cl. The phases were separated and the aqueous layer was extracted with Et2O. The combined organic layers were dried over Na2SO4 and concentrated. The residue was purified by silica gel chromatography eluted with 5% EtOAc in Hexanes to provide 1.9 g of the title compound as a pale yellow oil used as such.

Workup

stirringThe reaction mixture was stirred for 2 hours at r.t.
customwas quenched with saturated aqueous NH4Cl
customThe phases were separated
extractionthe aqueous layer was extracted with Et2O
dry with materialThe combined organic layers were dried over Na2SO4
concentrationconcentrated
customThe residue was purified by silica gel chromatography
washeluted with 5% EtOAc in Hexanes

Sources & evidence

ORD record: ord-6658225fc79045b590504812534c4cec
Source dataset: uspto-grants-2006_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07144913B2

Reaction notes

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