2-Fluorobenzoic acid → HCID 178525691, compound

HRID 715576Notes

Reaction equation

HRID 715576 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C@H:8]2[CH2:13][CH2:12][C@H:11]([OH:14])[CH2:10][CH2:9]2)=[CH:4][CH:3]=1.[F:15][C:16]1[CH:24]=[CH:23][CH:22]=[CH:21][C:17]=1[C:18](O)=[O:19].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C>O1CCCC1>[F:15][C:16]1[CH:24]=[CH:23][CH:22]=[CH:21][C:17]=1[C:18]([O:14][C@H:11]1[CH2:12][CH2:13][C@@H:8]([C:5]2[CH:4]=[CH:3][C:2]([Br:1])=[CH:7][CH:6]=2)[CH2:9][CH2:10]1)=[O:19]

Participants

6

Reactant 4

HCID 99352-Fluorobenzoic acidHCID 11776TriphenylphosphineHCID 5363146Diisopropyl azodicarboxylateHCID 178521543HCID 178521543, compound

Product 1

HCID 178525691HCID 178525691, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

(trans)-4-(4-Bromophenyl)cyclohexanol (100 mg), 2-fluorobenzoic acid (130 mg) and triphenylphosphine (225 mg) are dissolved in tetrahydrofurane (2 mL), treated dropwise with diisopropylazodicarboxylate (170 μL) and the mixture is stirred for 12 hours. Then the mixture is partitioned between ethylacetate and saturated aqueous NaHCO3 solution. The organic phase is dried (MgSO4) and concentrated. The residue is chromatographed on silica gel (cyclohexane/ethyl acetate 99:1→70:30) to give the title compound. LC (method 1): tR=1.29 min; Mass spectrum (ESI+): m/z=399 [M+Na]+.

Workup

  1. customThen the mixture is partitioned between ethylacetate and saturated aqueous NaHCO3 solution
  2. dry with materialThe organic phase is dried (MgSO4)
  3. concentrationconcentrated
  4. customThe residue is chromatographed on silica gel (cyclohexane/ethyl acetate 99:1→70:30)

Sources & evidence

ORD record
ord-b2110236f82147889f8c88daab6990e1
Source dataset
uspto-grants-2015_11
Patent number
US09187477B2

Reaction notes

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