Isopropanol → Bromobenzene

HRID 963780Notes

Reaction equation

HRID 963780 reaction equation
[OH:1][C@@H:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Br:8])[C@@H:3]1[OH:9].C(O)(C)C.CCCCCC>C1(C)C=CC=CC=1>[OH:1][C@@H:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Br:8])[C@@H:3]1[OH:9].[Br:8][C:4]1[CH:5]=[CH:6][CH:7]=[CH:2][CH:3]=1

Participants

6

Reactant 3

HCID 3776IsopropanolHCID 8058HexaneHCID 11769339HCID 11769339, compound

Product 2

HCID 7961BromobenzeneHCID 11769339HCID 11769339, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

The resolved 3-substituted cis-diol (12) (Scheme 5, R1 =Br) was prepared by separation of (11), prepared as shown in Example 9, on a chiral phase HPLC column Chiralcel OJ (Daicel Industries), isopropanol (10) : hexane (90) (HPLC, Boyd, et al., J. Chem. Soc. Chem. Commun., 1993, p. 974), (-) isomer r.t.=20.1 min., (+) isomer r.t.=21.5 min., α=1.15. The identity of the (+) isomer was determined by co-injection of the authentic compound produced by reaction of bromobenzene with toluene dioxygenase. The separated peaks were collected and their purity was confirmed by chromatography in the same system. The 1H NMR (DMSO, D6, 300 MHz) spectra of the separated compounds were identical to each other and the authentic (+) isomer.

Workup

  1. customprepared
  2. customisomer r.t.=20.1 min.
  3. customisomer r.t.=21.5 min., α=1.15

Sources & evidence

ORD record
ord-53601df27f1e4c24b4ab072e580cf91b
Source dataset
uspto-grants-1998_06
Patent number
US05763689

Reaction notes

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