Methyl iodide → Methyl 5-bromo-1-methyl-2,3-dihydro-1H-indene-1-carboxylate

HRID 2046555Notes

Reaction equation

C[Si]([N-][Si](C)(C)C)(C)C.[Li+].[CH3:11][O:12][C:13]([CH:15]1[C:23]2[C:18](=[CH:19][C:20]([Br:24])=[CH:21][CH:22]=2)[CH2:17][CH2:16]1)=[O:14].I[CH3:26]>C1COCC1>[CH3:11][O:12][C:13]([C:15]1([CH3:26])[C:23]2[C:18](=[CH:19][C:20]([Br:24])=[CH:21][CH:22]=2)[CH2:17][CH2:16]1)=[O:14]

Participants

Conditions

Temperature: -78 °C

Procedure

Lithium bis(trimethylsilyl)amide (6.16 ml, 6.16 mmol, 1M solution in THF) was added dropwise to a solution of (rac)-5-bromo-indan-1-carboxylic acid methyl ester (1.31 g, 5.14 mmol) in dry THF (25 ml) at −78° C. After the addition was completed, the solution was stirred at −78° C. for 45 minutes. Then, iodomethane (2.19 g, 959 μl, 15.4 mmol) was added, the solution was allowed to warm to room temperature and stirred for 48 h. The reaction was quenched by addition of sat. NH4Cl solution and extracted two times with EtOAc. The combined organic layers were washed with brine, dried with Na2SO4 and evaporated. The remaining yellow oil was purified by chromatography (silica gel; heptane/EtOAc 95:5) to obtain the title compound as yellow oil (1.319 g, 95%). MS: 269.2 [M+H]+.

Workup

additionAfter the addition
temperatureto warm to room temperature
stirringstirred for 48 h
customThe reaction was quenched by addition of sat. NH4Cl solution
extractionextracted two times with EtOAc
washThe combined organic layers were washed with brine
dry with materialdried with Na2SO4
customevaporated
customThe remaining yellow oil was purified by chromatography (silica gel; heptane/EtOAc 95:5)

Sources & evidence

ORD record: ord-708f1d7cb6334aa4a012cc8157bc2c14
Source dataset: uspto-grants-2013_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08592426B2

Reaction notes

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