Ethyl orthoformate → 1-Bromo-2-(diethoxymethyl)benzene

HRID 1085852Notes

Reaction equation

HRID 1085852 reaction equation
[Br:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1C=O.[CH:10]([O:17][CH2:18][CH3:19])([O:14][CH2:15][CH3:16])OCC>C(O)C.[Cl-].[NH4+]>[CH2:18]([O:17][CH:10]([O:14][CH2:15][CH3:16])[C:3]1[CH:6]=[CH:7][CH:8]=[CH:9][C:2]=1[Br:1])[CH3:19]

Participants

5

Reactant 2

HCID 31214Ethyl orthoformateHCID 811292-Bromobenzaldehyde

Product 1

HCID 34827781-Bromo-2-(diethoxymethyl)benzeneYield 66.7%

Reagents, catalysts & solvents 2

HCID 25517Ammonium ChlorideCatalystHCID 702EthanolSolvent

Procedure

A mixture of 2-bromobenzaldehyde (33.2 g), triethyl orthoformate (29 g) and powdered ammonium chloride (0.379 g) in ethanol (30 ml) was stirred for eight hours at room temperature. The resulting suspension was filtered and the filtrate evaporated. The resulting yellow oil was distilled at reduced pressure to give the title compound (31 g). b.p. 63° C. 0.3 mm Hg. T.l.c. (Petrol/diethyl ether, 6:1) Rf=0.6.

Workup

  1. filtrationThe resulting suspension was filtered
  2. customthe filtrate evaporated
  3. distillationThe resulting yellow oil was distilled at reduced pressure

Sources & evidence

ORD record
ord-68c2a93d044840bab95c346e79fcbbbe
Source dataset
uspto-grants-1991_04
Patent number
US05011848

Reaction notes

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