trans-2-(4-Bromo-3-fluorophenoxy)cyclopentanol → (1R,2R)-2-(4-bromo-3-fluorophenoxy)cyclopentyl acetate

HRID 2060813Notes

Reaction equation

HRID 2060813 reaction equation
[C:1]([O:4][C@@H:5]1[CH2:10][CH2:9][CH2:8]C[C@H:6]1[O:11][C:12]1[CH:17]=[CH:16][C:15]([Br:18])=[CH:14][CH:13]=1)(=[O:3])[CH3:2].BrC1C=CC(O[C@@H]2CCC[C@H]2O)=CC=1[F:33]>>[C:1]([O:4][C@@H:5]1[CH2:10][CH2:9][CH2:8][C@H:6]1[O:11][C:12]1[CH:13]=[CH:14][C:15]([Br:18])=[C:16]([F:33])[CH:17]=1)(=[O:3])[CH3:2]

Participants

3

Reactant 2

HCID 67192636trans-2-(4-Bromo-3-fluorophenoxy)cyclopentanolHCID 67197945(1R,2R)-2-(4-bromophenoxy)cyclohexyl acetate

Product 1

HCID 67196580(1R,2R)-2-(4-bromo-3-fluorophenoxy)cyclopentyl acetate

Procedure

The title compound in Step 2 was prepared according to the general procedure for the synthesis of (1R,2R)-2-(4-bromophenoxy)cyclohexyl acetate in Example 7, except that trans-2-(4-bromo-3-fluorophenoxy)cyclopentanol was used instead of trans-2-(4-bromophenoxy)cyclohexanol. The less polar material from the chromatographic purification on silica gel provided (1R,2R)-2-(4-bromo-3-fluorophenoxy)cyclopentyl acetate as an oil. Yield: 6.42 g, 20.2 mmol, 48% over 2 steps. 1H NMR (400 MHz, CDCl3) δ 1.67-1.75 (m, 1H), 1.79-1.92 (m, 3H), 2.05-2.20 (m, 2H), 2.08 (s, 3H), 4.60 (m, 1H), 5.14 (m, 1H), 6.66 (ddd, J=8.9, 2.8, 1.1 Hz, 1H), 6.78 (dd, J=10.5, 2.8 Hz, 1H), 7.40 (dd, J=8.8, 8.1 Hz, 1H).

Workup

  1. customThe less polar material from the chromatographic purification on silica gel

Sources & evidence

ORD record
ord-b55ab6b0fbe14f5c829612de862240fd
Source dataset
uspto-grants-2012_10
Patent number
US08278457B2

Reaction notes

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