Sodium Hydroxide → HCID 19862672, compound

HRID 1165278Notes

Reaction equation

HRID 1165278 reaction equation
[BH4-].[Na+].Br[CH2:4][C:5]([C:7]1[CH:12]=[CH:11][C:10]([O:13][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[C:9]([F:21])[CH:8]=1)=[O:6].[OH-].[Na+]>O1CCOCC1.CO.O>[F:21][C:9]1[CH:8]=[C:7]([CH:5]2[CH2:4][O:6]2)[CH:12]=[CH:11][C:10]=1[O:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

7

Reactant 3

HCID 14798Sodium HydroxideHCID 4311764Sodium borohydrideHCID 19862694HCID 19862694, compound

Product 1

HCID 19862672HCID 19862672, compoundYield 100.4%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolvent2×HCID 312751,4-DioxaneSolvent

Procedure

Sodium borohydride (1.25 g) was added in portions to a stirred solution of 2-bromo-1-[3-fluoro-4-(phenylmethoxy)phenyl]ethanone (16.6 g) in dioxan (100 ml) and methanol (100 ml) at 0°. After 0.5 h a solution of sodium hydroxide (4.0 g) in water (20 ml) was added and the mixture stirred for a further 1 h at 0°. Water was added and the mixture extracted with EA. The extracts were dried and evaporated to give the title compound as a colourless oil (12.6 g) which partially solidified on standing, t.l.c. (PE-EA 6:4) Rf 0.40.

Workup

  1. extractionthe mixture extracted with EA
  2. customThe extracts were dried
  3. customevaporated

Sources & evidence

ORD record
ord-5ddfaf1222784d9584ae84a749ce0f20
Source dataset
uspto-grants-1990_03
Patent number
US04908386

Reaction notes

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