Hydrochloric Acid → HCID 118006008, compound

HRID 1049625Notes

Reaction equation

HRID 1049625 reaction equation
[H-].C([Al+]CC(C)C)C(C)C.[Br:11][C:12]1[CH:21]=[C:20]([F:22])[CH:19]=[C:18]2[C:13]=1[CH:14]=[CH:15][C:16]([C:23](OC)=[O:24])=[CH:17]2.Cl>C1(C)C=CC=CC=1.C1COCC1>[Br:11][C:12]1[CH:21]=[C:20]([F:22])[CH:19]=[C:18]2[C:13]=1[CH:14]=[CH:15][C:16]([CH2:23][OH:24])=[CH:17]2

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 21225700DiisobutylaluminumhydrideHCID 118006063HCID 118006063, compound

Product 1

HCID 118006008HCID 118006008, compoundYield 98%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent

Procedure

1.0 M diisobutylaluminium hydride in toluene (11.5 mL) was slowly added to a solution of 30 (1.3 g, 4.6 mmol) in THF (15 mL) at −78° C. After the addition was completed, the mixture was allowed to warm to room temperature and continuously stirred for 18 h. The mixture was poured in to HCl aqueous solution (0.5 N, 50 mL) and extracted in ethyl acetate (2×100 mL). The combined organic layer was dried over anhydrous Na2SO4, filtered, concentrated rotary evaporation, and purified by column chromatography to give (5-bromo-7-fluoronaphthalen-2-yl)methanol (31) (98%). 1H NMR (400 MHz, CDCl3) δ 8.19 (d, J=8.8 Hz, 1H), 7.77 (s, 1H), 7.59 (d, J=8.2 Hz, 1H), 7.53 (d, J=9.0 Hz, 1H), 7.45 (d, J=11.4 Hz, 1H), 4.90 (s, 2H). GC-MS (ES) for C11H8BrFO [M+1]+ 255.

Workup

  1. additionAfter the addition
  2. extractionextracted in ethyl acetate (2×100 mL)
  3. dry with materialThe combined organic layer was dried over anhydrous Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated rotary
  6. customevaporation
  7. custompurified by column chromatography

Sources & evidence

ORD record
ord-118524c113f64769b6309e038b9c42a2
Source dataset
uspto-grants-2016_07
Patent number
US09382245B2

Reaction notes

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