2-Bromo-1-(thiophen-2-yl)ethan-1-one → HCID 22324999, compound

HRID 2419206Notes

Reaction equation

HRID 2419206 reaction equation
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]([CH2:8][Br:9])=[O:7].[BH4-].[Na+]>CO>[Br:9][CH2:8][CH:6]([C:2]1[S:1][CH:5]=[CH:4][CH:3]=1)[OH:7]

Participants

4

Reactant 2

HCID 27763722-Bromo-1-(thiophen-2-yl)ethan-1-oneHCID 4311764Sodium borohydride

Product 1

HCID 22324999HCID 22324999, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Conditions

Temperature
0 °C

Procedure

A solution of the haloketone, bromomethyl 2-thienyl ketone (6.0 g), described in Example 3, in 40 ml of methanol is cooled to 0° C. Sodium borohydride (1.11 g) in 10 ml of methanol is added rapidly to the solution. After 15 minutes the reaction mixture is diluted with ice-water and extracted with ether. The extract is washed with water and brine, dried (MgSO4) and concentrated to give α-(bromomethyl)-2-thiophenemethanol; γmaxCHCl3 3550, 3400, 1060, 1035 cm-1 (ArCHOHCHR2Y; Ar = 2-thienyl, R2 = H and Y = Br).

Workup

  1. extractionextracted with ether
  2. washThe extract is washed with water and brine
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-3c205a13ffe848d78143c71b0732766c
Source dataset
uspto-grants-1978_08
Patent number
US04105663

Reaction notes

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