Bromomethyl methyl ether → HCID 21252632, compound

HRID 1530784Notes

Reaction equation

HRID 1530784 reaction equation
C([C:3]1[CH:28]=[CH:27][CH:26]=[CH:25][C:4]=1[C:5]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1[OH:24])([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=C.BrCOC>C(Cl)Cl.[Br-].C([N+](CC)(CC)CC)C1C=CC=CC=1>[C:4]1([C:5]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)([C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=2[OH:24])[CH:3]=[CH:28][CH:27]=[CH:26][CH:25]=1

Participants

5

Reactant 2

HCID 83093Bromomethyl methyl etherHCID 70118057HCID 70118057, compound

Product 1

HCID 21252632HCID 21252632, compound

Reagents, catalysts & solvents 2

HCID 165294Benzyltriethylammonium bromideCatalystHCID 6344DichloromethaneSolvent

Procedure

The 2-(vinyltrityl)phenol (1.0 equiv.) is dissolved in CH2Cl2/50% KOH/H2O. Benzyltriethyl ammonium bromide is added as a phase transfer agent (0.1 equiv.). To this two phase mixture is added bromomethylmethylether (MOMBr). The reaction is allowed to stir for 30 minutes. The organic phase is separated, washed with water and brine before being dried with MgSO4. Solvent is removed to yield the MOM-protected 2-triphenylmethylphenol in near quantitative yield.

Workup

  1. customThe organic phase is separated
  2. washwashed with water and brine
  3. dry with materialbefore being dried with MgSO4
  4. customSolvent is removed

Sources & evidence

ORD record
ord-6f81d81d9af444e6b186cdf6706f1947
Source dataset
uspto-grants-2001_03
Patent number
US06197715B1

Reaction notes

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