5-Bromo-benzo(b)thiophene-2-carboxylic acid → (5-Bromo-benzo[b]thiophen-2-yl)-methanol

HRID 1173821

Reaction equation

HRID 1173821 reaction equation
[Br:1][C:2]1[CH:13]=[CH:12][C:5]2[S:6][C:7]([C:9](O)=[O:10])=[CH:8][C:4]=2[CH:3]=1>C1COCC1>[Br:1][C:2]1[CH:13]=[CH:12][C:5]2[S:6][C:7]([CH2:9][OH:10])=[CH:8][C:4]=2[CH:3]=1

Participants

3

Reactant 1

HCID 7377375-Bromo-benzo(b)thiophene-2-carboxylic acid

Product 1

HCID 21844218(5-Bromo-benzo[b]thiophen-2-yl)-methanolYield 51.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

Dissolve 5-bromo-benzo[b]thiophene-2-carboxylic acid (21.2 g, 82.5 mmol) in THF (150 mL). Cool to 0° C. with an ice bath. Add 2M BH3 dimethyl sulfide complex in THF (82.5 mL). Stir to room temperature over 2 hours. Quench by careful addition of water. Partition between ether and saturated NaHCO3, wash with water, brine, dry, and concentrate. Purify via column chromatography eluting with 3:1 hexanes:ethyl acetate to afford a white solid (10.3 g): 1H NMR (CDCl3) δ 7.87 (m, 1H), 7.67 (d, 1H), 7.41 (dd, 1H), 7.15 (m, 1H), 4.94 (d, 2H), 1.91 (t, 1H).

Workup

  1. customQuench by careful addition of water
  2. customPartition between ether and saturated NaHCO3
  3. washwash with water, brine
  4. customdry
  5. concentrationconcentrate
  6. customPurify via column chromatography
  7. washeluting with 3:1 hexanes

Sources & evidence

ORD record
ord-47624e7d3ee545ba976f65ea6d9ccd53
Source dataset
uspto-grants-2010_11
Patent number
US07834194B2

Linked notes

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