Triphenylphosphine → {4-[8-Bromomethyl-2,2,4,4-tetramethyl-chroman-6-ylethynyl]-phenyl}-acetic acid methyl ester

HRID 898677Notes

Reaction equation

HRID 898677 reaction equation
[CH3:1][O:2][C:3](=[O:29])[CH2:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]#[C:12][C:13]2[CH:14]=[C:15]3[C:20](=[C:21]([CH2:23]O)[CH:22]=2)[O:19][C:18]([CH3:26])([CH3:25])[CH2:17][C:16]3([CH3:28])[CH3:27])=[CH:7][CH:6]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Br:49]N1C(=O)CCC1=O>ClCCl>[CH3:1][O:2][C:3](=[O:29])[CH2:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]#[C:12][C:13]2[CH:14]=[C:15]3[C:20](=[C:21]([CH2:23][Br:49])[CH:22]=2)[O:19][C:18]([CH3:26])([CH3:25])[CH2:17][C:16]3([CH3:28])[CH3:27])=[CH:7][CH:6]=1

Participants

5

Reactant 3

HCID 11776TriphenylphosphineHCID 67184N-bromobutanimideHCID 59692069{4-[8-Hydroxymethyl-2,2,4,4-tetramethyl-chroman-6-ylethynyl]-phenyl}-acetic acid methyl ester2×

Product 1

HCID 59692064{4-[8-Bromomethyl-2,2,4,4-tetramethyl-chroman-6-ylethynyl]-phenyl}-acetic acid methyl esterYield 80%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A stirred, cooled (ice bath) solution of {4-[8-hydroxymethyl-2,2,4,4-tetramethyl-chroman-6-ylethynyl]-phenyl}-acetic acid methyl ester (Compound 46, 0.53 g, 0.58 mmol) and triphenylphosphine (0.198 g, 0.75 mmol) in anhydrous dichloromethane (5 mL) was treated with N-bromo succinimide (0.134 g, 0.75 mmol) under argon and the resulting reaction mixture was allowed to warm to ambient temperature and stirred overnight. The reaction mixture was quenched with dilute, aqueous sodium bicarbonate solution and extracted with diethyl ether. The organic phase was washed with water and brine, dried over anhydrous magnesium sulfate, filtered and evaporated in vacuo to a residue that on flash column chromatography over silica gel (230-400 mesh) using 4-10% ethyl acetate in hexane as the eluent afforded the title compound (0.19 g, 80%) as a colorless oil.

Workup

  1. customthe resulting reaction mixture
  2. customThe reaction mixture was quenched
  3. additionwith dilute
  4. extractionaqueous sodium bicarbonate solution and extracted with diethyl ether
  5. washThe organic phase was washed with water and brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. filtrationfiltered
  8. customevaporated in vacuo to a residue that on flash column chromatography over silica gel (230-400 mesh)

Sources & evidence

ORD record
ord-a54d0c92ce964f6596d9e49f61f44d03
Source dataset
uspto-grants-2008_04
Patent number
US07351737B2

Reaction notes

Loading…