2-Bromo-4-chloro-1-fluorobenzene → HCID 57812727, compound

HRID 912051Notes

Reaction equation

HRID 912051 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[F:9].BrC1[C:16]([CH:17]([OH:19])C)=C(Cl)C(F)=CC=1>>[Br:1][C:2]1[C:3]([F:9])=[CH:4][CH:5]=[C:6]([Cl:8])[C:7]=1[CH:17]([OH:19])[CH3:16]

Participants

3

Reactant 2

HCID 27732642-Bromo-4-chloro-1-fluorobenzeneHCID 57812482HCID 57812482, compound

Product 1

HCID 57812727HCID 57812727, compound

Procedure

Starting from 2-bromo-4-chloro-1-fluorobenzene, the procedure for 1-(6-bromo-2-chloro-3-fluorophenyl)ethanol was followed, except column chromatography required a less polar solvent system for product elution (CH2Cl2:Heptane 3:1→1:0→neat EtOAc). Additionally, preparative TLC purification was also required to obtain pure product. 1H NMR (400 MHz, CDCl3) δ=1.65 (d, J=6.8 Hz, 3H), 2.98 (br s, 1H), 5.59 (q, J=6.8 Hz, 1H), 7.01 (dd, J=8.7, 7.5 Hz, 1H), 7.32 (dd, J=8.7, 4.9 Hz, 1H). MS (ES+): m/z 275.99/277.96 [MNa+]. HPLC: tR=3.23 min (ZQ3, polar—5 min).

Workup

  1. washfor product elution (CH2Cl2:Heptane 3:1→1:0→neat EtOAc)
  2. customAdditionally, preparative TLC purification
  3. customto obtain pure product
  4. custom5 min

Sources & evidence

ORD record
ord-f537831fc95c45f798d68e23100fcbb8
Source dataset
uspto-grants-2011_09
Patent number
US08022206B2

Reaction notes

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