Water → HCID 22010155, compound

HRID 322994Notes

Reaction equation

[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([C:15](=[O:23])[CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH:12]=[CH:13][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(NC(C)C)(C)C.[Li].[Br:32]Br.O>O1CCCC1.ClCCl>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([C:15](=[O:23])[CH:16]([Br:32])[C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)[CH:12]=[CH:13][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Conditions

Temperature: -70 °C

Procedure

A stirred solution of 1-(3-benzyloxyphenyl)-2-phenylethanone in tetrahydrofuran (30 mL) is treated with a solution of lithium diisopropylamine in tetrahydrofuran (5.5 mL, 2 M) at −35° C. under nitrogen. The resulting clear yellow solution is cooled to −70° C. and treated with a solution of bromine (1.6 g) in dichloromethane (5 mL). Stirring is continued at −70° C. and treated with a solution of bromine (1.6 g) in dichloromethane (5 mL). Stirring is continued at −70° C. for 5 minutes. Water (30 mL) is added and the reaction mixture allowed to warm to room temperature. The reaction mixture is extracted twice with ether (50 mL), the combined extracts are washed with brine (40 mL), dried over magnesium sulphate and evaporated to give (RS)-1-(3-benzyloxyphenyl)-2-bromo-2-phenylethanone (3.92 g) in the form of a yellow oil.

Workup

customis continued at −70° C.
stirringStirring
temperatureto warm to room temperature
extractionThe reaction mixture is extracted twice with ether (50 mL)
washthe combined extracts are washed with brine (40 mL)
dry with materialdried over magnesium sulphate
customevaporated

Sources & evidence

ORD record: ord-19f05323c5764598bd713f3becfbcbb8
Source dataset: uspto-grants-2001_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06211234B1

Reaction notes

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