Bromine → HCID 178521543, compound

HRID 715564

Reaction equation

[C:1]1([C@H:7]2[CH2:12][CH2:11][C@H:10]([OH:13])[CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Al+3].[Cl-].[Cl-].[Cl-].[Br:18]Br>ClCCl>[Br:18][C:4]1[CH:5]=[CH:6][C:1]([C@H:7]2[CH2:8][CH2:9][C@H:10]([OH:13])[CH2:11][CH2:12]2)=[CH:2][CH:3]=1

Participants

Conditions

Temperature: -8 °C

Procedure

(trans)-4-Phenylcyclohexanol (2 g) is dissolved in dichloromethane (40 mL) and cooled to −8° C. AlCl3 (3 g) is added portionwise and the mixture is stirred for further 15 minutes after addition is complete. Then a solution of bromine (1.87 mL) in dichloromethane (10 mL) is added dropwise. The mixture is stirred for 10 minutes and is then partitioned between dichloromethane and ice-water. Concentrated hydrochloric acid (20 mL) is added, the phases are separated and the aqueous phase is extracted 3 times with dichloromethane. The combined organic phases are dried (Na2SO4) and concentrated. The residue is chromatographed on silica gel (cyclohexane/ethyl acetate 2:1) to give the title compound. TLC: rf=0.3 (silicagel, cyclohexane/ethylacetate 2:1).

Workup

additionafter addition
stirringThe mixture is stirred for 10 minutes
customis then partitioned between dichloromethane and ice-water
additionConcentrated hydrochloric acid (20 mL) is added
customthe phases are separated
extractionthe aqueous phase is extracted 3 times with dichloromethane
dry with materialThe combined organic phases are dried (Na2SO4)
concentrationconcentrated
customThe residue is chromatographed on silica gel (cyclohexane/ethyl acetate 2:1)

Sources & evidence

ORD record: ord-13cc272b1f2243d1a74331530ec24fba
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09187477B2

Linked notes

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