Water → 1-Adamantan-2-yl-3-(4-hydroxy-2-methyl-phenyl)-urea

HRID 1259036Notes

Reaction equation

[CH:1]12[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH:2]1[NH:11][C:12]([NH:14][C:15]1[CH:20]=[CH:19][C:18]([O:21]C)=[CH:17][C:16]=1[CH3:23])=[O:13])[CH2:8]2.B(Br)(Br)Br.O>C(Cl)Cl>[CH:1]12[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH:2]1[NH:11][C:12]([NH:14][C:15]1[CH:20]=[CH:19][C:18]([OH:21])=[CH:17][C:16]=1[CH3:23])=[O:13])[CH2:8]2

Participants

Conditions

Temperature: -78 °C

Procedure

To a suspension of 1-adamantan-2-yl-3-(4-methoxy-2-methyl-phenyl)-urea 1.56 g (4.88 mmol) in DCM 20 ml was added at −78° C. under argon a solution of boron tribromide 1M in DCM 14.67 ml (14.67 mmol). The reaction mixture was stirred at −78° C. for 1 h then allowed to reach room temperature. Water 60 ml was added, the precipitate was filtered, washed with water and dried under vacuum to give 1.36 g (92%) a white solid.

Workup

customto reach room temperature
filtrationthe precipitate was filtered
washwashed with water
customdried under vacuum

Sources & evidence

ORD record: ord-000a76d4b01b45f1a2e5c700b079f56f
Source dataset: uspto-grants-2013_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08466200B2

Reaction notes

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