Carbon tetrabromide → HCID 67351737, compound

HRID 1672658Notes

Reaction equation

HRID 1672658 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.Br[C:21]([Br:24])(Br)Br.[F:25][C:26]1[CH:27]=[CH:28][C:29]([O:34][CH2:35][C:36]#[C:37][C:38]2[CH:43]=[CH:42][C:41]([C:44]([F:47])([F:46])[F:45])=[CH:40][CH:39]=2)=[C:30](CO)[CH:31]=1>C1COCC1>[F:25][C:26]1[CH:27]=[CH:28][C:29]([O:34][CH2:35][C:36]#[C:37][C:38]2[CH:43]=[CH:42][C:41]([C:44]([F:45])([F:46])[F:47])=[CH:40][CH:39]=2)=[C:30]([CH:31]=1)[CH2:21][Br:24]

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 57864412HCID 57864412, compound

Product 1

HCID 67351737HCID 67351737, compoundYield 24%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

834 mg (3.18 mmol) of triphenylphosphine and 1.05 g (3.18 mmol) of tetrabromomethane are dissolved in 2 ml of THF and stirred at room temperature for 10 min. Then 860 mg (2.63 mmol) of {5-fluoro-2-[3-(4-trifluoromethylphenyl)prop-2-ynyloxy]phenyl}methanol, dissolved in 2 ml of THF, are added dropwise, and the mixture is stirred at room temperature overnight. The solvent is distilled out in vacuo, and the residue is chromatographed on silica gel (mobile phase: cyclohexane/ethyl acetate 10:1). 240 mg (0.62 mmol, 24% of theory) of 5-fluoro-2-[3-(4-trifluoromethylphenyl)prop-2-ynyloxy]benzyl bromide are obtained.

Workup

  1. additionare added dropwise
  2. stirringthe mixture is stirred at room temperature overnight
  3. distillationThe solvent is distilled out in vacuo
  4. customthe residue is chromatographed on silica gel (mobile phase: cyclohexane/ethyl acetate 10:1)

Sources & evidence

ORD record
ord-e3c00f85b93e48aa9df1d3bd646fe5f3
Source dataset
uspto-grants-2011_08
Patent number
US07998988B2

Reaction notes

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