1,5-Dibromopentane → 1-(2-Amino-5-bromo-phenyl)cyclohexanol

HRID 50683

Reaction equation

[NH2:1][C:2]1[CH:10]=[CH:9][C:8]([Br:11])=[CH:7][C:3]=1[C:4]([OH:6])=O.Br[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17]Br>>[NH2:1][C:2]1[CH:10]=[CH:9][C:8]([Br:11])=[CH:7][C:3]=1[C:4]1([OH:6])[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1

Participants

Reactant 2

HCID 81001,5-Dibromopentane

HCID 798582-Amino-5-bromobenzoic acid

Product 1

HCID 235096031-(2-Amino-5-bromo-phenyl)cyclohexanol

Procedure

Prepared according to the procedure of Example 1 from 2-amino-5-bromobenzoic acid and the Grignard reagent prepared from 1,5-dibromopentane A clear oil: 1H-NMR (DMSO-d6) δ 7.07 (d, 1H, J=2.3 Hz), 7.03 (dd, 1H, J=8.4, 2.4 Hz), 6.55 (d, 1H, J=8.6 Hz), 5.49 (s, 2H, H2O exchangeable), 5.00. (s, 1H, D2O exchangeable), 2.01 (d, 2H, J=1.8 Hz), 1.66-1.77 (m, 2H), 1.44-1.61 (m, 4H), 1.16-1.34 (m, 2H). MS (ESI) m/z 270/272 ([M+H]+, 98%/100%).

Workup

customPrepared

Sources & evidence

ORD record: ord-4c255192d5294d8999d0d94a0526788a
Source dataset: uspto-grants-2004_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06713478B2

Linked notes

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