Methanol → HCID 20260932, compound

HRID 1583351Notes

Reaction equation

HRID 1583351 reaction equation
B.O1CCCC1.[Br:7][C:8]1[S:12][C:11]2[CH:13]=[C:14]([C:17](O)=[O:18])[CH:15]=[CH:16][C:10]=2[C:9]=1[CH3:20].B.CO>O1CCCC1>[Br:7][C:8]1[S:12][C:11]2[CH:13]=[C:14]([CH2:17][OH:18])[CH:15]=[CH:16][C:10]=2[C:9]=1[CH3:20]

Participants

6

Reactant 4

HCID 887MethanolHCID 6331BoraneHCID 2723981Borane;tetrahydrofuranHCID 20260918HCID 20260918, compound

Product 1

HCID 20260932HCID 20260932, compoundYield 82.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of borane-tetrahydrofuran complex (150 ml. of 1M solution in THF) was added dropwise with stirring to a solution of 2-bromo-3-methylbenzo[b]thiophene-6-carboxylic acid (7.32 g.) in dry tetrahydrofuran (120 ml.) at 0° C. under an atmosphere of dry nitrogen. The solution was stirred at room temperature for 4 hours and then the excess borane was decomposed by the cautious addition of methanol. The solution was evaporated and the residue was dissolved in ether. The solution was washed with water, dried (Na2SO4) and evaporated to give a solid which was crystallized from ether/petrol (b.p. 40°-60°) to give 2-bromo-6-hydroxymethyl-3-methylbenzo[b]thiophene (5.70 g.), m.p. 91° C.

Workup

  1. customThe solution was evaporated
  2. dissolutionthe residue was dissolved in ether
  3. washThe solution was washed with water
  4. dry with materialdried (Na2SO4)
  5. customevaporated
  6. customto give a solid which
  7. customwas crystallized from ether/petrol (b.p. 40°-60°)

Sources & evidence

ORD record
ord-2c0fc03a5d114322a86e62dd2b57b107
Source dataset
uspto-grants-1985_11
Patent number
US04551468

Reaction notes

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