Water → 2-(Bromomethyl)-3-chloro-1-benzothiophene

HRID 576936

Reaction equation

HRID 576936 reaction equation
[Cl:1][C:2]1[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[S:4][C:3]=1[CH2:11]O.P(Br)(Br)[Br:14].O>C(OCC)C>[Br:14][CH2:11][C:3]1[S:4][C:5]2[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=2[C:2]=1[Cl:1]

Participants

5

Reactant 3

HCID 962WaterHCID 24614Phosphorus tribromideHCID 821965(3-Chloro-1-benzothien-2-yl)methanol

Product 1

HCID 8167082-(Bromomethyl)-3-chloro-1-benzothiophene

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

To a solution of (3-chloro-1-benzothiophen-2-yl)methanol (480 mg, 2.4 mmol) in anhydrous diethyl ether (8 mL) was added dropwise a solution of phosphorus tribromide (230 μL, 2.4 mmol) in anhydrous diethyl ether (2 mL) at 0° C. The mixture was stirred for 3 hours at room temperature. Water was added and extracted 3 times with ethyl acetate. The combined organic phase was washed with brine and dried over magnesium sulfate. After evaporation of the solvent, 2-(bromomethyl)-3-chloro-1-benzothiophene was obtained as a pink pale solid (537 mg, 85% yield) and used for the next step without further purification; 1H NMR (400 MHz, CDCl3): δ 4.81 (s, 2H), 7.40-7.48 (m, 2H), 7.76-7.82 (m, 2H).

Workup

  1. extractionextracted 3 times with ethyl acetate
  2. washThe combined organic phase was washed with brine
  3. dry with materialdried over magnesium sulfate
  4. customAfter evaporation of the solvent

Sources & evidence

ORD record
ord-a02e62eea5164712a3ce5b589e66f62e
Source dataset
uspto-grants-2015_05
Patent number
US09040538B2

Linked notes

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