Water → Methyl 4-(Bromomethyl)-2-[(tert-butyldimethylsilyl)oxy]benzoate

HRID 217440Notes

Reaction equation

[Si:1]([O:8][C:9]1[CH:18]=[C:17]([CH3:19])[CH:16]=[CH:15][C:10]=1[C:11]([O:13][CH3:14])=[O:12])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].C1C(=O)N([Br:27])C(=O)C1.CC(N=NC(C#N)(C)C)(C#N)C.O>C(Cl)(Cl)(Cl)Cl>[Br:27][CH2:19][C:17]1[CH:16]=[CH:15][C:10]([C:11]([O:13][CH3:14])=[O:12])=[C:9]([O:8][Si:1]([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:2])[CH3:3])[CH:18]=1

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of methyl 2-{[tert-butyl(dimethyl)silyl]oxy}-4-methylbenzoate (3.4 g) in carbon tetrachloride (68 mL) were added, and NBS (2.16 g) and AIBN (398 mg) were added thereto at room temperature, followed by stirring at 80° C. for 1 hour. Completion of the reaction was confirmed by means of TLC, and to the reaction liquid was added water to stop the reaction, followed by extraction with EtOAc. The organic layer was washed with brine, dried using MgSO4, and then concentrated under reduced pressure, followed by purification by silica gel column chromatography (automatic purification device, hexane:EtOAc=100:0 to 95:5) to obtain methyl 4-(bromomethyl)-2-{[tert-butyl(dimethyl)silyl]oxy}benzoate (3.79 g) as a colorless liquid.

Workup

customat room temperature
customto the reaction liquid
customthe reaction
extractionfollowed by extraction with EtOAc
washThe organic layer was washed with brine
customdried
concentrationconcentrated under reduced pressure
customfollowed by purification by silica gel column chromatography (automatic purification device, hexane:EtOAc=100:0 to 95:5)

Sources & evidence

ORD record: ord-0f7d09ec63144a56b65de87ea9d3cf80
Source dataset: uspto-grants-2012_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08193378B2

Reaction notes

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